Acetic Acid → 2-chloro-N-[2-methoxy-5-(trifluoromethyl)phenyl]-acetamide

HRID 35322

Reaction equation

HRID 35322 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[NH2:13].C(O)(=O)C.[Cl:18][CH2:19][C:20](Cl)=[O:21].C([O-])(=O)C.[Na+]>O>[Cl:18][CH2:19][C:20]([NH:13][C:4]1[CH:5]=[C:6]([C:9]([F:11])([F:10])[F:12])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[O:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6577Chloroacetyl chlorideHCID 517045Sodium AcetateHCID 6006372-Methoxy-5-(trifluoromethyl)aniline

Product 1

HCID 142302752-chloro-N-[2-methoxy-5-(trifluoromethyl)phenyl]-acetamideYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled (about 10° C.) solution of 11.7 parts of 2-methoxy-5-(trifluoromethyl)benzenamine in 50 parts of acetic acid were added dropwise 7.7 parts of chloroacetyl chloride at a temperature below 20° C. After stirring for 30 minutes, there was added dropwise a solution of 24.8 parts of sodium acetate in 62 parts of water (exothermic reaction). Upon completion, stirring was continued for 30 minutes at room temperature. The precipitated product was filtered off, washed with a lot of water and dried, yielding 15.5 parts (93.3%) of 2-chloro-N-[2-methoxy-5-(trifluoromethyl)phenyl]-acetamide; mp. 94.7° C. (intermediate 62).

Workup

  1. stirringAfter stirring for 30 minutes
  2. stirringUpon completion, stirring
  3. filtrationThe precipitated product was filtered off
  4. washwashed with a lot of water
  5. customdried

Sources & evidence

ORD record
ord-377a94b0686f4107959ba1575d2f4d81
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Linked notes

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