Acetonitrile → HCID 10444178, compound

HRID 1180712Notes

Reaction equation

HRID 1180712 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])=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:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[N:5]=[C:3]([Cl:32])[C:2]([F:15])([F:14])[F:1]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 75654Diphenyl chlorophosphateHCID 529465HCID 529465, compound

Product 1

HCID 10444178HCID 10444178, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
82 °C

Procedure

Five grams (22.8 mmol) of 2,2,2-trifluoro-N-(2-methoxyphenyl)acetamide, 12.24 g (45.6 mmol) of diphenyl chlorophosphate, 4.64 g (45.6 mmol) of triethylamine, and 25 ml of acetonitrile were introduced into a 100 ml flask and reacted for 22.5 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 4.55 g of N-(2-methoxyphenyl)-2,2,2-trifluoroacetimidoyl chloride as a yellow liquid (yield: 84.3%).

Workup

  1. customreacted for 22.5 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-6558fb17e98a4f41ba6675be42303b7c
Source dataset
uspto-grants-2007_10
Patent number
US07282609B2

Reaction notes

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