Methanol → 2-Chloro-N,4-dimethyl-5-thiazolesulfonamide

HRID 2301269Notes

Reaction equation

HRID 2301269 reaction equation
[CH3:1][NH2:2].CO.[Cl:5][C:6]1[S:7][C:8]([S:12](Cl)(=[O:14])=[O:13])=[C:9]([CH3:11])[N:10]=1.O>ClCCl>[Cl:5][C:6]1[S:7][C:8]([S:12]([NH:2][CH3:1])(=[O:14])=[O:13])=[C:9]([CH3:11])[N:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6329MethylamineHCID 120942502-Chloro-4-methyl-1,3-thiazole-5-sulfonyl chloride

Product 1

HCID 114246772-Chloro-N,4-dimethyl-5-thiazolesulfonamideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

177 ml of a solution of methylamine in methanol (2 M, 0.354 mol) are added at 0° C. to a solution of 41 g (0.177 mol) of 2-chloro-4-methyl-1,3-thiazole-5-sulphonyl chloride in 360 ml of dichloromethane. The mixture is stirred at 0° C. for 30 min, 1.8 l of water are added, and the mixture is extracted 5 times with 400 ml of dichloromethane each time. The combined organic phases are dried over sodium sulphate, and the solvent is distilled off. 39.93 g of an oil, which solidifies on standing, are obtained (Rf=0.43 (toluene/ethyl acetate=2/1), yield 99.7%)

Workup

  1. extractionthe mixture is extracted 5 times with 400 ml of dichloromethane each time
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. distillationthe solvent is distilled off
  4. customare obtained (Rf=0.43 (toluene/ethyl acetate=2/1), yield 99.7%)

Sources & evidence

ORD record
ord-d6c06887645f4e79bb7ad9dadc27fa0f
Source dataset
uspto-grants-2002_12
Patent number
US06500817B1

Reaction notes

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