Thionyl Chloride → 5-Chloro-4-chloromethyl-3-(4-chloro-phenyl)-1-phenyl-1H-pyrazole

HRID 441862Notes

Reaction equation

HRID 441862 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:7]=1[CH2:24]O>C1C=CC=CC=1>[Cl:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:7]=1[CH2:24][Cl:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 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-pyrazoleYield 98.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

17.6 g of thionyl chloride are added to a suspension of 45 g of 5-chloro-3-p-chlorophenyl-4-hydroxymethyl-1-phenyl-pyrazole in 45 ml of benzene, there being a considerable evolution of gas and solution occurs. Following this heating is carried out for 30 minutes at boiling point for completion of the reaction. The solvent is distilled off in vacuo and this operation is carried out with the addition of benzene. The residue is caused to crystallise with the help of petroleum ether. 5-Chloro-4-chloromethyl-3-p-chlorophenyl-1-phenyl-pyrazole is obtained with a 98.5% yield; F 96.5°-97°.

Workup

  1. customfor completion of the reaction
  2. distillationThe solvent is distilled off in vacuo
  3. additionthis operation is carried out with the addition of benzene
  4. customto crystallise with the help of petroleum ether

Sources & evidence

ORD record
ord-7b2a46b886984b9887a6a7f3b04ffcae
Source dataset
uspto-grants-1977_08
Patent number
US04042702

Reaction notes

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