Electric Literature of 61881-19-4,Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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.
10249] To a solution of 6-(6?-azidohexyl)-2,3,4-tri-O-ben- zyl-a/3-D-galactopyranose 18 (400 mg, 0.70 mmol) in CH2C12 (7 mE) was added cesium carbonate (340 mg, 1.04 mmol). To the mixture was added 2,2,2-trifluoro-N-pheny- lacetimidoyl chloride 24 (216 mg, 1.04 mmol) and the reaction mixture was stirred at r.t. for 3.5 h after which it was filtered over celite and washed with CH2C12. The solvent was removed in vacuo and the crude product was purified by flash column chromatography on silica gel (gradient hexanes/ EtOAc1 0:1 – 1:1) to yield the imidate 19 (490 mg, 94%) as a colorless oil. [a]Dt+60.8 (c0.4, CHC13); R1O.8O (Hexanes/EtOAc 2:1); IR (film) vm,x 3064, 2934, 2865, 2094, 1717, 1598, 1454, 1321, 1207, 1099, 1027, 910, 734, 696cm?; ?H NMR (400 MHz, CDC13) oe 7.45-6.60 (m, 20H),5.56 (s, 1H), 4.90 (d, J11.5 Hz, 1H), 4.75 (s, J1.5 Hz, 2H),4.68 (s, J12.4 Hz, 2H), 4.58 (d, J11.6 Hz, 1H), 4.00 (t,J8.7 Hz, 1H), 3.84 (d, J2.4 Hz, 1H), 3.58-3.39 (m, 4H),3.34 (dt, J9.3, 6.5 Hz, 1H), 3.23 (dt, J9.3, 6.5 Hz, 1H), 3.14(t, J6.9 Hz, 2H), 1.52-1.38 (m, 4H), 1.32-1.16 (m, 4H); ?3CNMR (101 MHz, CDC13) oe 138.6, 138.3, 138.2, 128.8, 128.6,128.5, 128.4, 128.4, 128.3, 128.0, 127.9, 127.8, 127.7, 124.3,119.4,82.3,78.3,77.4,77.2,76.8,75.7,74.9,74.6,73.4,73.2,71.4, 68.7, 51.5, 29.7, 28.9, 26.7, 25.8; HR ESI Calcd forC41H45F3N406 [M+Na]: 769.3183. found: 769.3239.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, its application will become more common.
Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; UNIVERSITAeTSSPITAL BASEL; Seeberger, Peter H.; Stallforth, Pierre; De Libero, Gennaro; Cavallari, Marco; US2015/238597; (2015); A1;,
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