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

HRID 2059080Notes

Reaction equation

HRID 2059080 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][NH:6][CH:7]=1.[OH-].[Na+].O.[Cl:11][CH2:12][C:13]([N:15]([CH2:24]Cl)[C:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:23])=[O:14]>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:11][CH2:12][C:13]([N:15]([CH2:24][N:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:7]=[N:6]1)[C:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:23])=[O:14]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 53247764-methoxy-1H-pyrazoleHCID 130698822-Chloro-N-(chloromethyl)-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 205090252-chloro-2',6'-dimethyl-N-(4-methoxypyrazol-1-yl-methyl)acetanilide

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 1140TolueneSolvent

Procedure

A solution of 10.8 parts by weight of 4-methoxypyrazole and 4.0 parts by weight of sodium hydroxide in 20 parts by volume of water was added dropwise at 10°-15° C., with vigorous stirring, to a solution of 24.6 parts by weight of 2-chloro-N-chloromethyl-2',6'-dimethylacetanilide and one part by weight of benzyltriethylammonium bromide in 70 parts by volume of toluene and the stirring was continued for 3 hours. The organic phase was washed with three times 40 parts by volume of water, dried over sodium sulfate and evaporated in vacuo at 80° C. to give 28.1 parts by weight of 2-chloro-2',6'-dimethyl-N-(4-methoxypyrazol-1-yl-methyl)acetanilide of melting point 115°-116° C. (melting point of a sample recrystallized from ethanol: 118° C.), which according to the 1H-NMR spectrum and thin layer chromatography carried out using a 3:7 mixture of ethyl acetate:toluene was more than 97% pure.

Workup

  1. washThe organic phase was washed with three times 40 parts by volume of water
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo at 80° C.

Sources & evidence

ORD record
ord-767ab451c85e4f43aa5a7dbae6a93dec
Source dataset
uspto-grants-1982_03
Patent number
US04321395

Reaction notes

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