Hydrochloric Acid → 5-Chloro-4-chloromethyl-3-(4-chloro-phenyl)-1-phenyl-1H-pyrazole

HRID 441863Notes

Reaction equation

HRID 441863 reaction equation
[ClH:1].[Cl:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:4]=1[CH2:21]O>C1(C)C=CC=CC=1>[Cl:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:4]=1[CH2:21][Cl:1]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 53664379[5-Chloro-3-(4-chloro-phenyl)-1-phenyl-1H-pyrazol-4-yl]-methanol

Product 1

HCID 540260095-Chloro-4-chloromethyl-3-(4-chloro-phenyl)-1-phenyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Hydrogen chloride gas is introduced into a mixture of 15 g of 5-chloro-3-p-chlorophenyl-4-hydroxymethyl-1-phenylpyrazole and 25 ml of concentrated hydrochloric acid and heating is carried out for 4 hours at boiling point. Following this 25 ml of toluene are mixed in. The layers are separated and the aqueous phase with toluene is removed. The organic layers are reduced in bulk by evaporation in vacuo, toluene is again added and reduction in bulk is repeated. 5-Chloro-4-chloromethyl-3-p-chlorophenyl-1-phenyl-pyrazole is obtained with a quantitative yield; F 96.5°-97° (from petroleum ether).

Workup

  1. temperatureheating
  2. additionare mixed in
  3. customThe layers are separated
  4. customthe aqueous phase with toluene is removed
  5. customThe organic layers are reduced in bulk by evaporation in vacuo, toluene
  6. additionis again added

Sources & evidence

ORD record
ord-fb8e36b3867845e98cdf966d99d0f169
Source dataset
uspto-grants-1977_08
Patent number
US04042702

Reaction notes

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