Ammonium Hydroxide → 2-Chloro-4-methyl-1,3-thiazole-5-sulfonamide

HRID 1750749Notes

Reaction equation

HRID 1750749 reaction equation
[Cl:1][C:2]1[S:3][C:4]([S:8](Cl)(=[O:10])=[O:9])=[C:5]([CH3:7])[N:6]=1.[OH-].[NH4+:13]>C(O)(C)C>[Cl:1][C:2]1[S:3][C:4]([S:8]([NH2:13])(=[O:10])=[O:9])=[C:5]([CH3:7])[N:6]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 120942502-Chloro-4-methyl-1,3-thiazole-5-sulfonyl chloride

Product 1

HCID 120942512-Chloro-4-methyl-1,3-thiazole-5-sulfonamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-chloro-4-methylthiazole-5-sulfonyl chloride (1.0 g) in isopropyl alcohol (10 mL) was cooled with an ice-bath. Then, ammonium hydroxide (2.89 ml) was added slowly. The resulting solution was stirred at ambient temperature overnight. The solution was concentrated, the residue was mixed with water (10 mL) and extracted with ethyl acetate (2×20 mL). The crude product was purified on a silica gel column eluting with 60% ethyl acetate-hexane.

Workup

  1. concentrationThe solution was concentrated
  2. additionthe residue was mixed with water (10 mL)
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. customThe crude product was purified on a silica gel column
  5. washeluting with 60% ethyl acetate-hexane

Sources & evidence

ORD record
ord-eef337d5ecf64eb3b62c4f3853101dd8
Source dataset
uspto-grants-2015_10
Patent number
US09156856B2

Reaction notes

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