4-Methylpyrazole → 2-chloro-2',6'-dimethyl-N-(4-methylpyrazol-1-yl-methyl)-acetanilide

HRID 2059079Notes

Reaction equation

HRID 2059079 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[OH-].[Na+].[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].[Br-].C([P+](CCCC)(CCCC)C)CCC>ClC1C=CC=CC=1Cl.O>[Cl:9][CH2:10][C:11]([N:13]([CH2:22][N:4]1[CH:3]=[C:2]([CH3:1])[CH:6]=[N:5]1)[C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])=[O:12]

Participants

7

Reactant 4

HCID 34064-MethylpyrazoleHCID 14798Sodium HydroxideHCID 130698822-Chloro-N-(chloromethyl)-N-(2,6-dimethylphenyl)acetamideHCID 22168974Tri-n-butylmethylphosphonium bromide

Product 1

HCID 133243652-chloro-2',6'-dimethyl-N-(4-methylpyrazol-1-yl-methyl)-acetanilide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 9.0 parts by weight of 4-methylpyrazole and 4.0 parts by weight of sodium hydroxide in 20 parts by volume of water was added dropwise at 0° C., with vigorous stirring, to a solution of 24.6 parts by weight of 2-chloro-N-chloromethyl-2',6'-dimethylacetanilide and 0.15 part by weight of tri-n-butylmethylphosphonium bromide in 80 parts by volume of o-dichlorobenzene, and the stirring was continued for 5 hours at 10° C. The organic phase was washed with three times 50 parts by volume of water, dried over sodium sulfate and evaporated under reduced pressure at 70° C. to give 25.6 parts by weight of 2-chloro-2',6'-dimethyl-N-(4-methylpyrazol-1-yl-methyl)-acetanilide of melting point 100° C.; the product was pure according to the 1H-NMR spectrum and according to thin layer chromatography carried out using a 3:7 ethyl acetate:toluene mixture.

Workup

  1. washThe organic phase was washed with three times 50 parts by volume of water
  2. dry with materialdried over sodium sulfate
  3. customevaporated under reduced pressure at 70° C.

Sources & evidence

ORD record
ord-64cb9e10d7214ccaae665c6763f48704
Source dataset
uspto-grants-1982_03
Patent number
US04321395

Reaction notes

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