Chloroacetyl chloride → 2-Chloro-2'-difluoromethoxy-6'-methylacetanilide

HRID 542655Notes

Reaction equation

HRID 542655 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=1[NH2:6].C(=O)([O-])[O-].[K+].[K+].[Cl:19][CH2:20][C:21](Cl)=[O:22]>CC(C)=O>[Cl:19][CH2:20][C:21]([NH:6][C:5]1[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:4]=1[O:3][CH:2]([F:12])[F:1])=[O:22]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 189816732-(Difluoromethoxy)-6-methylaniline

Product 1

HCID 202064612-Chloro-2'-difluoromethoxy-6'-methylacetanilideYield 94.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The procedures of Example 3 were repeated except that the starting material was 50 ml of an acetone solution containing 8.9 g (51 mmol) of 2-difluoromethoxy-6-methyl aniline, to which 10.5 g (77 mmol) of potassium carbonate and 7.0 g (62 mmol) of chloroacetyl chloride were added. As a result, 12.0 g of 2-chloro-2'-difluoromethoxy-6'-methylacetanilide was obtained. It had a melting point of 85° to 86° C.

Sources & evidence

ORD record
ord-e49dd8794c0d4766af0f0d5d85feb4eb
Source dataset
uspto-grants-1987_04
Patent number
US04659365

Reaction notes

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