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

HRID 1413101Notes

Reaction equation

HRID 1413101 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[CH2:14]O.S(Cl)([Cl:18])=O>>[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[CH2:14][Cl:18]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 940312(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 49627755-chloro-4-(chloromethyl)-3-methyl-1-phenyl-1H-pyrazole

Procedure

6.1 g of 5-chloro-4-hydroxymethyl-3-methyl-1-phenylpyrazole are added portionwise to 50 ml of thionylchloride. The mixture is refluxed for 2 hours, the excess thionylchloride distilled off, the oily product treated with water and then extracted with ether. The dried ethereal extract is evaporated in vacuo yielding 6.1 g of oily 5-chloro-4-chloromethyl-3-methyl-1-phenylpyrazole which, without further purification, is used in the next reaction step.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. distillationthe excess thionylchloride distilled off
  3. additionthe oily product treated with water
  4. extractionextracted with ether
  5. extractionThe dried ethereal extract
  6. customis evaporated in vacuo

Sources & evidence

ORD record
ord-388b9d62d787454981ddacf6ae52855f
Source dataset
uspto-grants-1981_02
Patent number
US04248881

Reaction notes

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