Pyridine → HCID 86648442, compound

HRID 2094790Notes

Reaction equation

HRID 2094790 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[Cl:10])[NH2:6].N1C=CC=CC=1.[Cl:19][C:20]([Cl:25])([Cl:24])[C:21](Cl)=[O:22]>ClCCl>[Cl:19][C:20]([Cl:25])([Cl:24])[C:21]([NH:6][C:5]1[CH:7]=[CH:8][C:9]([Cl:10])=[C:3]([C:2]([F:1])([F:11])[F:12])[CH:4]=1)=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 675744-Chloro-3-(trifluoromethyl)aniline

Product 1

HCID 86648442HCID 86648442, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The clear solution of 3-trifluoromethyl-4-chloroaniline (45 g, 0.230 mol) and pyridine (37 ml, 0.460 mol) in dichloromethane (450 ml) cooled at 0° C. to −5° C. and a solution of trichloroacetyl chloride (31 ml, 0.2876 mol) in dichloromethane (100 ml) was added drop wise maintaining temperature of the reaction mass below 0° C. The reaction mass was then stirred for 1 hour below 0° C. and quenched with water (250 ml) below 5° C. The organic phase was separated and aqueous layer was re-extracted with dichloromethane. The combined dichloromethane layer was washed with water, dried over sodium sulfate and evaporated under vacuum to obtain (62 g) of the desired product, i.e., 2,2,2-trichloro-N-(4-chloro-3-(trifluoromethyl)phenyl)acetamide.

Workup

  1. temperaturewise maintaining temperature of the reaction mass below 0° C
  2. customquenched with water (250 ml) below 5° C
  3. customThe organic phase was separated
  4. extractionaqueous layer was re-extracted with dichloromethane
  5. washThe combined dichloromethane layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-13278e18e6284852b1662eda2fe5f79e
Source dataset
uspto-grants-2013_05
Patent number
US08445687B2

Reaction notes

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