Water → HCID 19436771, compound

HRID 260972Notes

Reaction equation

HRID 260972 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[F:19])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].C(Cl)Cl.O.[Cl:24][S:25](O)(=[O:27])=[O:26]>>[Cl:18][C:15]1[CH:14]=[C:13]([F:19])[C:12]([C:3]2[C:2]([Cl:1])=[C:6]([C:7]([F:8])([F:9])[F:10])[N:5]([CH3:11])[N:4]=2)=[CH:17][C:16]=1[S:25]([Cl:24])(=[O:27])=[O:26]

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24638Chlorosulfonic acidHCID 19436770HCID 19436770, compound

Product 1

HCID 19436771HCID 19436771, compoundYield 63%

Procedure

A solution of 4-chloro-3-(4-chloro-2-fluorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole in 20 mL of chlorosulfonic acid was heated in a 120° C. oil bath for four hours and allowed to cool to room temperature. Methylene chloride was added and the solution added dropwise to a stirring mixture of ice and water (caution, extremely reactive). The layers were separated and the aqueous layer was washed with methylene chloride. The combined organic layers were dried with MgSO4, filtered and concentrated and the resultant solid residue washed with a very small amount of ether and recrystallized from hexanes to afford 1.65 g (63%) of 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzenesulfonyl chloride as a white solid; mp 116°-117° C.

Workup

  1. customThe layers were separated
  2. washthe aqueous layer was washed with methylene chloride
  3. dry with materialThe combined organic layers were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washthe resultant solid residue washed with a very small amount of ether
  7. customrecrystallized from hexanes

Sources & evidence

ORD record
ord-d64cb38f8a6346188db0a9e1bfb5932b
Source dataset
uspto-grants-1996_06
Patent number
US05530126

Reaction notes

Loading…