Acetonitrile → HCID 10243436, compound

HRID 1180714Notes

Reaction equation

HRID 1180714 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=O.P([Cl:31])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.C(N(CC)CC)C.C(#N)C>C(OCC)(=O)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([N:5]=[C:3]([Cl:31])[C:2]([F:14])([F:13])[F:1])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 9830Acetanilide, 4'-chloro-2,2,2-trifluoro-HCID 75654Diphenyl chlorophosphate

Product 1

HCID 10243436HCID 10243436, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
82 °C

Procedure

Four grams (17.9 mmol) of 2,2,2-trifluoro-N-(4-chlorophenyl)acetamide, 9.61 g (35.8 mmol) of diphenyl chlorophosphate, 3.62 g (35.8 mmol) of triethylamine, and 20 ml of acetonitrile were introduced into a 50 ml flask and reacted for 16 hours while being refluxed (82° C.). After the reaction, the reaction solution was cooled to room temperature, 16 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 3.40 g of N-(4-chlorophenyl)-2,2,2-trifluoroacetimidoyl chloride as a yellow liquid (yield: 78.6%).

Workup

  1. customreacted for 16 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-37234f631a154a48bcd61bd4047f8e70
Source dataset
uspto-grants-2007_10
Patent number
US07282609B2

Reaction notes

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