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

HRID 1503099Notes

Reaction equation

HRID 1503099 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]([F:26])([F:25])[C:22](O)=O.C(N(CC)CC)C.[CH3:34][O:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1.C(Cl)(Cl)(Cl)[Cl:44]>>[F:20][C:21]([F:26])([F:25])[C:22]([Cl:44])=[N:40][C:39]1[CH:41]=[CH:42][C:36]([O:35][CH3:34])=[CH:37][CH:38]=1

Participants

6

Reactant 5

HCID 5943Carbon Tetrachloride2×HCID 6422Trifluoroacetic acidHCID 7732P-AnisidineHCID 8471TriethylamineHCID 11776Triphenylphosphine

Product 1

HCID 104216822,2,2-Trifluoro-N-(4-methoxyphenyl)acetimidoyl Chloride

Conditions

Temperature
0 °C

Procedure

In a typical reaction, a mixture of about 3 equivalents of triphenylphosphine and trifluoroacetic acid in carbon tetrachloride is cooled to about 0° C. in an ice bath and a 20% excess of triethylamine is added. With continued cooling, about a 20% excess of p-methoxyaniline in carbon tetrachloride is slowly added. After completion of the addition, the mixture is heated to about 70° C. for several hours. After cooling, the reaction mixture is extracted with hexane and the solvent evaporated to provide crude 2,2,2-trifluoro-N-(4-methoxyphenyl)acetimidoyl chloride.

Workup

  1. customIn a typical reaction
  2. additionis slowly added
  3. additionAfter completion of the addition
  4. temperaturethe mixture is heated to about 70° C. for several hours
  5. temperatureAfter cooling
  6. extractionthe reaction mixture is extracted with hexane
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-bb89b0cf70c54064b0bc199ef52c8182
Source dataset
uspto-grants-2015_12
Patent number
US09212141B2

Reaction notes

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