Water → Metazachlor

HRID 2059082Notes

Reaction equation

HRID 2059082 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[OH-].[Na+].O.[Cl:9][CH2:10][C:11]([N:13]([CH2:22]Cl)[C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])=[O:12]>C1(C)C=CC=CC=1>[Cl:9][CH2:10][C:11]([N:13]([CH2:22][N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1)[C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 14798Sodium HydroxideHCID 130698822-Chloro-N-(chloromethyl)-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 49384Metazachlor

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 7.5 parts by weight of pyrazole and 4.0 parts by weight of sodium hydroxide in 20 parts by volume of water was added dropwise at 20°-25° C., with vigorous stirring, to a solution of 24.6 parts by weight of 2-chloro-N-chloromethyl-2',6'-dimethylacetanilide and M parts by weight of phase transfer catalyst in 70 parts by volume of toluene, and stirring was continued for 3-5 hours at the same temperature. After complete conversion (checked by thin layer chromatography), the organic phase was washed three times with water, dried and concentrated under reduced pressure at 70° to give G parts by weight of 2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide, as shown in the Table which follows.

Workup

  1. washAfter complete conversion (checked by thin layer chromatography), the organic phase was washed three times with water
  2. customdried
  3. concentrationconcentrated under reduced pressure at 70°

Sources & evidence

ORD record
ord-05afdc06429e4deaaf2b992baec583ca
Source dataset
uspto-grants-1982_03
Patent number
US04321395

Reaction notes

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