Acetonitrile → 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride
Reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.P([Cl:30])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.C(N(CC)CC)C.C(#N)C>C(OCC)(=O)C>[C:6]1([N:5]=[C:3]([Cl:30])[C:2]([F:13])([F:12])[F:1])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
6
Conditions
- Temperature
- 82 °C
Procedure
Seven grams (37.0 mmol) of 2,2,2-trifluoro-N-phenylacetamide, 19.84 g (74.0 mol) of diphenyl chlorophosphate, 7.44 g (74.0 mmol) of triethylamine, and 28 ml of acetonitrile were introduced into a 100 ml flask and reacted for 15 hours while being refluxed (82° C.). After the reaction, the reaction solution was cooled to room temperature, 28 ml of ethyl acetate was added thereto, and the precipitate was then filtered off. The filtrate was subjected to solvent removal by evaporation, and the crude product thus obtained was purified by column chromatography (silica gel, ethyl acetate:hexane=3:7), resulting in 6.24 g of N-phenyl-2,2,2-trifluoroacetimidoyl chloride as a yellow liquid (yield: 81.2%).
Workup
- customreacted for 15 hours
- customAfter the reaction
- temperaturethe reaction solution was cooled to room temperature
- filtrationthe precipitate was then filtered off
- customThe filtrate was subjected to solvent removal by evaporation
- customthe crude product thus obtained
- customwas purified by column chromatography (silica gel, ethyl acetate:hexane=3:7)
Sources & evidence
- ORD record
- ord-ac199f4e69b44cb890e0207fbf086ea4
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07282609B2
Reaction notes
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