Acetonitrile → HCID 11775698, compound

HRID 1180706Notes

Reaction equation

HRID 1180706 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[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>[CH3:12][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 75654Diphenyl chlorophosphateHCID 136175Acetamide, 2,2,2-trifluoro-N-(4-methylphenyl)-

Product 1

HCID 11775698HCID 11775698, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
82 °C

Procedure

Seven grams (34.5 mmol) of 2,2,2-trifluoro-N-(4-methylphenyl)acetamide, 18.49 g (68.9 mmol) of diphenyl chlorophosphate, 6.97 g (68.9 mmol) of triethylamine, and 35 ml of acetonitrile were introduced into a 100 ml flask and reacted for 18 hours while being refluxed (82° C.). After the reaction, the reaction solution was cooled to room temperature, 25 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 6.77 g of N-(4-methylphenyl)-2,2,2-trifluoroacetimidoyl chloride as a yellow liquid (yield: 88.6%).

Workup

  1. customreacted for 18 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-0adf829e6bd2401dabb239807a649bcb
Source dataset
uspto-grants-2007_10
Patent number
US07282609B2

Reaction notes

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