Ammonia → HCID 178432590, compound

HRID 1769291Notes

Reaction equation

HRID 1769291 reaction equation
[NH3:1].[Cl:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([Cl:13])[C:4]=1[C:14]1[NH:15][C:16]([S:20](Cl)(=[O:22])=[O:21])=[C:17]([CH3:19])[N:18]=1.O>O1CCOCC1>[Cl:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([Cl:13])[C:4]=1[C:14]1[NH:15][C:16]([S:20]([NH2:1])(=[O:22])=[O:21])=[C:17]([CH3:19])[N:18]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 178432591HCID 178432591, compound

Product 1

HCID 178432590HCID 178432590, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Aqueous ammonia solution (approximately33% w/w, 1.2 ml) was added dropwise with stirring to a solution of 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-methyl-imidazole-5-sulphonyl chloride (2.0 g, 0.005 mol) in dioxane (15 ml) and the mixture was stirred for 3 hours. It was poured into water (50 ml) and extracted with diethyl ether (3×25 ml). The combined extracts were washed with water (2×50 ml) dried over anhydrous sodium sulphate and evaporated to dryness. The residue was purified by mplc on silica eluted with.a mixture of ethyl acetate and petroleum spirit (bp 60°-80° C.) (1:2). Recrystallization from a mixture of ethyl acetate and petroleum spirit (b.p. 60°-80° C.) (1:3) gave 2-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-methylimidazole-5-sulphonamide (0.45 g), m.p. 266°-267° C., as an off-white solid.

Workup

  1. extractionextracted with diethyl ether (3×25 ml)
  2. washThe combined extracts were washed with water (2×50 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated to dryness
  5. customThe residue was purified by mplc on silica
  6. washeluted
  7. additionwith.a mixture of ethyl acetate and petroleum spirit (bp 60°-80° C.) (1:2)
  8. customRecrystallization
  9. additionfrom a mixture of ethyl acetate and petroleum spirit (b.p. 60°-80° C.) (1:3)

Sources & evidence

ORD record
ord-0d442a9e56844e9cb16ca97db74bf05b
Source dataset
uspto-grants-1995_01
Patent number
US05380865

Reaction notes

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