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

HRID 2059081Notes

Reaction equation

HRID 2059081 reaction equation
[CH:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([CH3:3])[CH3:2].[OH-].[K+].O.[Cl:12][CH2:13][C:14]([N:16]([CH2:25]Cl)[C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:24])=[O:15]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C(Cl)(Cl)Cl>[Cl:12][CH2:13][C:14]([N:16]([CH2:25][N:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:8]=[N:7]1)[C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:24])=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 130698822-Chloro-N-(chloromethyl)-N-(2,6-dimethylphenyl)acetamideHCID 200673214-(Propan-2-yl)-1H-pyrazole

Product 1

HCID 205484002-chloro-2',6'-dimethyl-N-(4-isopropylpyrazol-1-yl-methyl)-acetanilide

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 12.1 parts by weight of 4-isopropylpyrazole and 5.6 parts by weight of potassium hydroxide in 30 parts by volume of water was added at 25° C., with vigorous stirring, to a solution of 24.6 parts by weight of 2-chloro-N-chloromethyl-2',6'-dimethylacetanilide and 0.5 part by weight of triethylbenzylammonium chloride in 100 parts by volume of chloroform and stirring was continued for 4 hours at 25° 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 50° C. to give 26.2 parts by weight of 2-chloro-2',6'-dimethyl-N-(4-isopropylpyrazol-1-yl-methyl)-acetanilide of melting point 58° C.

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 50° C.

Sources & evidence

ORD record
ord-7d002f98fb0647f7ad448f1050b01232
Source dataset
uspto-grants-1982_03
Patent number
US04321395

Reaction notes

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