Trichloroacetyl chloride → HCID 12427466, compound

HRID 1156338Notes

Reaction equation

HRID 1156338 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].C(N(CC)CC)C.[Cl:18][C:19]([Cl:24])([Cl:23])[C:20](Cl)=[O:21]>C1C=CC=CC=1>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:20](=[O:21])[C:19]([Cl:24])([Cl:23])[Cl:18])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 110862'-Aminoacetophenone

Product 1

HCID 12427466HCID 12427466, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 13.5 parts of 1-(2-aminophenyl)ethanone, 12.1 parts of N,N-diethylethanamine and 72 parts of benzenes are stirred and cooled at 5°-10° C. Then there is added dropwise a solution of 18.2 parts of trichloroacetyl chloride in 36 parts of benzene while still cooling at 1°-10° C. Upon completion, stirring at that temperature is continued for 30 minutes. The reaction mixture is filtered, the filter-cake is washed with benzene and the filtrate is evaporated. The solid residue is boiled in methanol. After cooling, the product is filtered off and dried, yielding 19 parts (68%) of N-(2-acetylphenyl)-2,2,2-trichloroacetamide; mp. 112.7° C.

Workup

  1. temperaturecooled at 5°-10° C
  2. temperaturewhile still cooling at 1°-10° C
  3. stirringUpon completion, stirring at that temperature
  4. filtrationThe reaction mixture is filtered
  5. washthe filter-cake is washed with benzene
  6. customthe filtrate is evaporated
  7. temperatureAfter cooling
  8. filtrationthe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-736a6c71ac904b439e206500cb4f99a1
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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