Tag: M.W=100-200

Electric Literature of 106-39-8,Some common heterocyclic compound, 106-39-8, name is 1-Bromo-4-chlorobenzene, molecular formula is C6H4BrCl, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

At room temperature, to a suitable solvent(a mixture of 1-Sulfobutyl-3-methylimidazolium trifluoromethansulfonate and 1,4-dioxane of volume ration 1:8),add add 100 mmol compound of the above formula (1), 180 mmol compound of the above formula (II), 7 mmol of a catalyst (2mmol of Pd (TFA) 2 and 5 mmol of CuBr), 10mmol of the bipyridine organic ligand of formula L3 and 20 mmol of trifluoroacetic acid, and then the temperature was raised to 80 C and the reaction was stirred at this temperature for 4 hours. After the reaction, The resulting reaction system is cooled to room temperature and filtered filtrate is saturated with sodium bicarbonate aqueous solution till no bubble remain. The acetone was extracted and the organic phase was separated and dried over anhydrous magnesium sulfate and distilled under pressure, the resulting residue was purified by flash column chromatography (elution solvent mixture of petroleum ether and ethyl acetate in a volume ratio of 15: 1) to give a compound of formula (III) ,yield of 96.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-chlorobenzene, its application will become more common.

Reference:
Patent; Jiang Yulan; Li Meiling; Han Deyu; Zheng Xuemei; (10 pag.)CN105152826; (2017); B;,
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Electric Literature of 72235-56-4, A common heterocyclic compound, 72235-56-4, name is 3-Chloro-4-fluorobenzylamine, molecular formula is C7H7ClFN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a 50 mL shaker vessel was added 2,6-dimethoxy-4- polystyrenebenzyloxy-benzaldehyde (DMHB resin) (2 g, 1.5 mmol/g, 3 mmol) and 25 mL of NMP. 3-Chloro-4-fluorobenzylamine (1.92 g, 12 mmol), HOAc (2.5 mL, 10%), and Na (OAc) 3BH (3.18 g, 15 mmol) were then added. The mixture was shaken at rt for overnight. The resutling resin was washed with NMP (25 mL x 2), DCM (25 mL x 2), MeOH (25 mL x 2) and DCM (25 mL x 2) and dried in vacuum oven at 35 C for overnight to yield DMHB resin-bound 3-chloro-4- fluorobenzylamine.

The synthetic route of 72235-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/87236; (2005); A1;,
Chloride – Wikipedia,
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Related Products of 4584-46-7, The chemical industry reduces the impact on the environment during synthesis 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, I believe this compound will play a more active role in future production and life.

Solution of 2-(dimethylamino)ethyl chloride in heptane. To 2-(dimethylamino)ethyl chloride hydrochloride (10 g, 100 mmol) was added water (12 mL) and heptane (10 g). The mixture was stirred, and the pH of the aqueous phase was cautiously adjusted to pH 10 using a concentrated solution of sodium hydroxide, and the mixture was stirred for 45 min. The organic phase was separated, and the aqueous phase was extracted with further heptane (2.5 g). The combined organic phases were washed with water (5 mL) and then dried over anhydrous potassium carbonate for 15 min before filtering. This solution was used directly in the following step. Analysis by MR indicated that the concentration of 2- (dimethylamino)ethyl chloride was approximately 25 % w/w in heptane.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Chloro-N,N-dimethylethanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LUNDBECK A/S; B?GES?, Klaus, Peter; JUHL, Karsten; ZHONG, Huailing; L?LAND, Claus, Juul; WO2013/110313; (2013); A1;,
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Some common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 1871-57-4

To a cold (-78 C, acetone/solid CO2) and magnetically stirred solution of diisopropylamine (0.8 mL, 5.7 mmol) in anhydrous THF (15 mL) under an argon atmosphere, a solution of n-BuLi in hexanes (2.3 mL, 2.5 M, 5.7 mmol) was added dropwise.When n-BuLi addition was finished, the solution was allowed to warm to 0 C for 1 h, it was cooled again to -78 C, and a solution of 11 (690 mg, 2.38 mmol) in anhydrous THF (8 mL) was added dropwise. Then, the solution was stirred a -78 C for 15 min and allowed to warm to 0 C for 1 h. The solution was again cooled to -78 C and 3-chloro-2-(chloromethyl)-1-propene (0.36mL 96% content, 373 mg, 3.0 mmol) was added dropwise. The reaction mixture was allowed towarm to room temperature and it was stirred for 3 days at this temperature. The mixture was made acidic with aqueous 1N HCl (10 mL) and was extracted with Et2O (3¡Á50 mL). The combined organic extracts were dried (anhydrous Na2SO4) and concentrated in vacuo to give abrown waxy residue (960 mg) that was subjected to column chromatography (silica gel 35-70mum, 30 g, hexane/EtOAc mixtures) to give on elution with hexane/EtOAc 9:1, product 12 (515mg, 63% yield) as a yellow solid. Rf 0.51 (silica gel, 8 cm, hexane/EtOAc 8:2); mp 190-192 C (from EtOAc/hexane); IR (ATR, numax, cm-1): 1770w and 1693s (C=O st); 1H NMR (400 MHz,CDCl3) delta 1.65 (br s, H2O), 2.11 [dt, 2JHH 16.4 Hz, 4JHH 2.4 Hz, 2H, 16(18)-Hn], 2.47 (s, 3H, NCH3),2.64 [br d, 2JHH 16.4 Hz, 2H, 16(18)-Hx], 4.51 [s, 2H, 4(9)-H], 4.61-4.62 (br s, 2H,C17=CH2), 7.06-7.10 [m, 2H, 6(7)-H], 7.17-7.20 [m, 2H, 12(13)-H], 7.21-7.25 [m, 2H, 5(8)-H], 7.34-7.38 [m, 2H, 11(14)-H]; 13C NMR (100.6 MHz, CDCl3) delta 24.5 (CH3, N-CH3), 39.3[CH2, C16(18)], 49.5 [CH, C4(9)], 62.0 [C, C3a(9a)], 108.8 (CH2, C17=CH2), 124.9 [CH,C5(8)], 126.6 [CH, C11(14)], 126.81 [CH, C12(13)], 126.85 [CH, C6(7)], 139.6 [C, C4a(8a)],139.9 [C, C10(15)], 146.6 (C, C17), 180.1 [C, C1(3)]; HRMS (ESI-TOF): calcd. for[C23H19NO2+H]+: 342.1489. Found: 342.1485; Anal. calcd. for C23H19NO2¡¤0.25H2O: C, 79.86;H, 5.68; N, 4.05%. Found: C, 79.47; H, 5.62; N, 3.88%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1871-57-4, its application will become more common.

Reference:
Article; Camps, Pelayo; Gomez, Tania; Otermin, Ane; ARKIVOC; vol. 2014; 2; (2014); p. 103 – 119;,
Chloride – Wikipedia,
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Electric Literature of 4584-46-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4584-46-7 name is 2-Chloro-N,N-dimethylethanamine hydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of 4-hydroxybenzaldehyde (6.0 g, 49.1 mmol), 2-chloro-N,N- dimethylethanamine hydrochloride (10.61 g, 73.70 mmol) and potassium carbonate (20.37 g, 147.4 mmol) in N,N-dimethylformamide (60 mL) was stirred overnight at 90 C The solvent was evaporated and the residue partitioned between water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over sodium sulphate and the solvent evaporated to yield the title compound (7.25 g, 72%) as a brown oil. LRMS (m/z): 194 (M+1 )+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-N,N-dimethylethanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; ALMIRALL, S.A.; BACH TANA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/91531; (2015); A1;,
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Electric Literature of 1435-48-9, The chemical industry reduces the impact on the environment during synthesis 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, I believe this compound will play a more active role in future production and life.

To a warm solution of 1,3-dichloro-4-fluorobenzene at 70 C. (175.0 gm), anhydrous aluminum chloride was added in small portion with stirring (260.0 g). Then acetic anhydride was added in small portion with stirring (125 mL) followed by an additional amount of aluminum chloride (159.0 g). The temperature was slowly raised to 120 C. with stirring for 25 hours. The thick reaction mixture was cooled and poured into 400 cc of concentrated hydrochloric acid containing ice. The oil was extracted with methylene chloride, washed with water, dried over anhydrous magnesium sulfate and concentrated to give 165.0 g of oil (2).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,4-Dichloro-1-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Vymed Corporation; SHETTY, B. Vithal; US2014/73631; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H4ClNaO2S

General procedure: Pyrazoles 4 (0.5 mmol), sodium sulfinate 2 (1.0 mmol) and NBS or NIS (1.5 mmol) were dissolved in 2 mL of EtOAc solvent. the reaction mixture was stirred at room temperature under air for 12 h. After the reaction, the resulting mixture was extracted with EtOAc. The combined organic phase was dried over anhydrous Na2SO4 and the solvent was then removed under vacuum. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate, 3:1) to afford the corresponding product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 14752-66-0.

Reference:
Article; Fu, Lili; Bao, Xiaodong; Li, Shanshan; Wang, Lingtian; Liu, Zhiguo; Chen, Wanzhi; Xia, Qinqin; Liang, Guang; Tetrahedron; vol. 73; 17; (2017); p. 2504 – 2511;,
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32768-54-0, name is 2,3-Dichlorotoluene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C7H6Cl2

Example 14 endo-8-(2-Chloro-3-methyl-4-nitrophenyl)-8-azabicyclo[3.2.1]octan-3-ol (196MBT14-B) To a suspension of 2,3-dichlorotoluene (500 mg, 3.11 mmol) in concentrated sulfuric acid (2.5 mL) was added dropwise a solution of potassium nitrate (314 mg, 3.11 mmol) in concentrated sulfuric acid (2.5 mL) at room temperature. The resulting suspension was stirred 1 hour at room temperature and then poured into ice/water (100 mL) under stirring. The resulting aqueous phase was basified to pH 10 by addition of 25% aqueous ammonia and subsequently extracted with dichloromethane (2¡Á100 mL). The combined organic phases were dried over sodium sulphate, filtered and evaporated. The crude product was purified by preparative TLC (0-100% ethyl acetate in heptane) to give a 4:1 mixture of 6- and 5-nitrated product (232 mg). 80 mg of this mixture was dissolved in pyridine (1 mL). Nortropine (198 mg, 1.553 mmol) was added and the mixture was heated to 110 C. in a sealed flask for 20 hours and then concentrated. The residue was dissolved in 2 M HCl (20 mL) and extracted with dichloromethane (2¡Á20 mL). The combined organic phases were dried over Na2SO4, filtered and evaporated, and the resulting oil was purified by preparative TLC (eluting with dichloromethane) to afford the title compound (35 mg, 14% from 2,3-dichlorotoluene) as a yellow solid. LC/MS m/z 297 [M+H]+. 1H-NMR (CDCl3) delta 7.76 (d, J=10.5, 1H), 6.80 (d, J=10.5, 1H), 4.24-4.16 (m, 1H), 4.14-4.05 (m, 2H), 2.59 (s, 3H), 2.40-2.25 (m, 4H), 1.97-1.81 (m, 4H), 1.55 (s, 1H).

The synthetic route of 32768-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schlienger, Nathalie; Thygesen, Mikkel Boas; Pawlas, Jan; Badalassi, Fabrizio; Lewinsky, Rasmus; Lund, Birgitte Winther; Olsson, Roger; US2006/160845; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 20850-43-5, These common heterocyclic compound, 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Preparation of compound Ig: 2-(Benzo[l,3]dioxol-5-ylmethyl-methyI-amino)-ethanol. 2-(Methylamino)ethanol (22.0 g, 290 mmol) was added to a stirred solution of 3,4- methylenedioxybenzyl chloride (25.0 g, 147 mmol) in DCM (45 mL) at -780C under nitrogen. The solution was stirred for 15 minutes at -78 0C then warmed to room temperature and stirred for 16h. 1.2 M NaOH (100 mL) was added and the phases were separated. The organic layer was washed water (2 x 150 mL) and concentrated under vacuum to give 25.3 g (83%) of 2-(benzo[l,3]dioxol-5-ylmethyl- methyl-amino)-ethanol as a clear oil.

Statistics shows that 5-(Chloromethyl)benzo[d][1,3]dioxole is playing an increasingly important role. we look forward to future research findings about 20850-43-5.

Reference:
Patent; KALYPSYS, INC.; WO2007/62410; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-fluoroaniline, molecular formula is C6H5ClFN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 2106-02-7

General procedure: The synthesis of azides were carried out according to the publish procedure [59]. Briefly, aniline (1eq) was dissolved in6N HCl solution (10mL/mmol of aniline) at room temperature and cooled up to 0C, followed by addition of aqueous NaNO2 (1eq) solution under stirring. After 10min of stirring at same temperature, sodium azide (1.2eq) was added to the reaction mixture. This mixture was further stirred at room temperature for 2-3h. The reaction was worked up by extraction with chloroform. The organic layer was washed with brine solution and dried over Na2SO4. After evaporation of the solvent, the crude product (3a-r) was pure enough for further reactions. All the synthesized azides were stored at-20C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2106-02-7, its application will become more common.

Reference:
Article; Kant, Rama; Singh, Vishal; Nath, Gopal; Awasthi, Satish Kumar; Agarwal, Alka; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 218 – 228;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics