Pyridine → HCID 86648442, compound

HRID 2094774Notes

Reaction equation

HRID 2094774 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 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The clear solution of 3-trifluoromethyl-4-chloroaniline (35 g, 0.1789 mol) and pyridine (36 ml, 0.447 mol) in dichloromethane (350 ml) was cooled at 0° C. to −5° C. and a solution of trichloro acetyl chloride (26 ml, 0.2326 mol) in dichloromethane (75 ml) was added drop wise maintaining temperature of the reaction mass below 0° C. The reaction mass was stirred for 1 hour below 0° C. and quenched with water (150 ml) below 5° C. The organic phase was separated and aqueous layer was reextracted with dichloromethane. The combined dichloromethane layer was then washed with water, dried over sodium sulfate and evaporated under vacuum to obtain (55 g) 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 (150 ml) below 5° C
  3. customThe organic phase was separated
  4. washThe combined dichloromethane layer was then washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-617b6e10f0b14584b71669133678e6ab
Source dataset
uspto-grants-2013_05
Patent number
US08445687B2

Reaction notes

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