Carbon Tetrachloride → 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride

HRID 2189513Notes

Reaction equation

HRID 2189513 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.[C:27](O)([C:29]([F:32])([F:31])[F:30])=O.[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(Cl)(Cl)(Cl)[Cl:42]>>[F:30][C:29]([F:32])([F:31])[C:27]([Cl:42])=[N:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 5

HCID 5943Carbon Tetrachloride2×HCID 6115AnilineHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 11776Triphenylphosphine

Product 1

HCID 100588692,2,2-Trifluoro-N-phenylacetimidoyl Chloride

Procedure

A mixture of Ph3P (138.0 g, 526 mmol), Et3N (21.3 g, 211 mmol), CCl4 (170 mL) and TFA (20 g, 175 mmol) was stirred for 10 min in an ice-bath. Aniline (19.6 g, 211 mmol) was dissolved in CCl4 (20 mL) was added. The mixture was stirred at reflux for 3 h. The solvent was removed under vacuum and hexane was added. The precipitates (Ph3PO and Ph3P) were filtered off and washed with hexane. The filtrate was distilled under reduced pressure to yield 2,2,2-trifluoro-N-phenyl-acetimidoyl chloride (19 g), which was used in the next step without further purification.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred
  3. temperatureat reflux for 3 h
  4. customThe solvent was removed under vacuum and hexane
  5. additionwas added
  6. customThe precipitates (Ph3PO and Ph3P)
  7. filtrationwere filtered off
  8. washwashed with hexane
  9. distillationThe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-ac777193415b46ffad7b267809d7a57d
Source dataset
uspto-grants-2012_12
Patent number
US08324242B2

Reaction notes

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