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Acetonitrile → 2,2,2-Trifluoro-N-(4-methoxyphenyl)acetimidoyl Chloride

HRID 1180708
Notes
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Reaction equation

HRID 1180708 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=O.P([Cl:32])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.C(N(CC)CC)C.C(#N)C>C(OCC)(=O)C>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:5]=[C:3]([Cl:32])[C:2]([F:15])([F:14])[F:1])=[CH:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 75654Diphenyl chlorophosphateHCID 1012842,2,2-Trifluoro-N-(4-methoxy-phenyl)-acetamide

Product 1

HCID 104216822,2,2-Trifluoro-N-(4-methoxyphenyl)acetimidoyl ChlorideYield 83.6%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
82 °C

Procedure

Five grams (22.8 mmol) of 2,2,2-trifluoro-N-(4-methoxyphenyl)acetamide, 12.26 g (45.6 mmol) of diphenyl chlorophosphate, 4.62 g (45.6 mmol) of triethylamine, and 25 ml of acetonitrile were introduced into a 100 ml flask and reacted for 22 hours while being refluxed (82° C.). After the reaction, the reaction solution was cooled to room temperature, 20 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 4.53 g of N-(4-methoxyphenyl)-2,2,2-trifluoroacetimidoyl chloride as a yellow liquid (yield: 83.6%).

Workup

  1. customreacted for 22 hours
  2. customAfter the reaction
  3. temperaturethe reaction solution was cooled to room temperature
  4. filtrationthe precipitate was then filtered off
  5. customThe filtrate was subjected to solvent removal by evaporation
  6. customthe crude product thus obtained
  7. customwas purified by column chromatography (silica gel, ethyl acetate:hexane=3:7)

Sources & evidence

ORD record
ord-3c2b5ee234e94be79b90de46313a659e
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07282609B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes