Ammonia → HCID 178432590, compound

HRID 1591091Notes

Reaction equation

HRID 1591091 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 (approximately 33% w /w, 1.2 ml) was added dropwise with stirring to a solution of 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylimidazole-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-trifluoromethylphenyl)-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 with a mixture of ethyl acetate and petroleum spirit (bp 60°-80° C.) (1:2)
  7. customRecrystallization
  8. additionfrom a mixture of ethyl acetate and petroleum spirit (b.p. 60°-80° C.) (1:3)

Sources & evidence

ORD record
ord-3313e4df0b024514a5d59e2b9114f5c6
Source dataset
uspto-grants-1993_04
Patent number
US05206257

Reaction notes

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