Pyrazole → Metazachlor

HRID 1981602

Reaction equation

HRID 1981602 reaction equation
[Cl:1][CH2:2][C:3]([N:5]([CH2:14]Cl)[C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4].[NH:16]1[CH:20]=[CH:19][CH:18]=[N:17]1>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:5]([CH2:14][N:16]1[CH:20]=[CH:19][CH:18]=[N:17]1)[C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4]

Participants

4

Reactant 2

HCID 1048PyrazoleHCID 130698822-Chloro-N-(chloromethyl)-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 49384Metazachlor

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

43.9 parts by weight of 2-chloro-2',6'-dimethyl-N-chloromethyl acetanilide and 25.8 parts by weight of pyrazole are stirred for 7 hours at 90° C. in 120 parts by volume of toluene. After the mixture has cooled it is filtered, and the filtrate is washed 3 times with water, each time with 50 parts by volume, and dried over sodium sulfate. The solvent is evaporated and the residue pasted with 50 parts by volume of petroleum ether to give 39.1 parts by weight of 2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide, m.p.: 81° C.

Workup

  1. temperatureAfter the mixture has cooled it
  2. filtrationis filtered
  3. washthe filtrate is washed 3 times with water
  4. dry with materialeach time with 50 parts by volume, and dried over sodium sulfate
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-8adae3aea54c42aab829a92824e3ab1a
Source dataset
uspto-grants-1986_06
Patent number
US04593104

Linked notes

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