Thionyl Chloride → HCID 178432591, compound

HRID 1769292Notes

Reaction equation

HRID 1769292 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]1[NH:14][CH:15]=[C:16]([CH3:18])[N:17]=1.[Cl:19][S:20](O)(=[O:22])=[O:21].S(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]1[NH:14][C:15]([S:20]([Cl:19])(=[O:22])=[O:21])=[C:16]([CH3:18])[N:17]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 178430847HCID 178430847, compound

Product 1

HCID 178432591HCID 178432591, compound

Conditions

Temperature
100 °C

Procedure

2-(2,6-Dichloro-4-trifluoromethylphenyl)-4-methyl-imidazole (1.0 g, 0.0034 mol) was added portionwise to chlorosulphonic acid (3 ml) and the mixture was stirred and heated at 100° C. for 2 hours. After cooling thionyl chloride (0.2 ml) was added and the mixture was reheated to 100° C. for 2 hours. The mixture was added cautiously to ice (20 g), and extracted with ethyl acetate (2×20 ml). The combined extracts were washed with water (20 ml) dried over anhydrous sodium sulphate and evaporated to dryness. Recystallisation from a mixture of ethyl acetate and petroleum spirit (bp 60°-80° C.) (1:3) gave 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylimidazole-5-sulphonyl chloride (0.21 g), m.p. 227°-230° C. as an off-white solid.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. washThe combined extracts were washed with water (20 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to dryness
  6. additionRecystallisation from a mixture of ethyl acetate and petroleum spirit (bp 60°-80° C.) (1:3)

Sources & evidence

ORD record
ord-5b7f85d1c3624db8b6cb398cbe0cc8c2
Source dataset
uspto-grants-1995_01
Patent number
US05380865

Reaction notes

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