Methanesulfonic Acid → 5-Phenyl-2-thiazole sulfonamide

HRID 440319Notes

Reaction equation

HRID 440319 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][N:13]=1)(=[O:8])=[O:7])(C)(C)C.CS(O)(=O)=O>ClCCCl>[C:14]1([C:11]2[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[N:13][CH:12]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22406990N-t-butyl-5-phenyl-2-thiazole sulfonamide

Product 1

HCID 224069645-Phenyl-2-thiazole sulfonamideYield 75%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of N-t-butyl-5-phenyl-2-thiazole sulfonamide (0.25 g, 0.84 mmol) in 17 mL of 1,2-dichloroethane was added methanesulfonic acid (0.11 mL, 1.68 mmol). The reaction was heated at reflux for 6.5 h and then concentrated. The product was subjected to flash chromatography (2:1 hexane/ethyl acetate). Recrystallization from ethyl acetate/hexane afforded 0.15 g (0.63 mmol, 63%) of 5-phenyl-2-thiazole sulfonamide (white crystals).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 6.5 h
  3. concentrationconcentrated
  4. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-270d515183b74ae88f963ad278d0d3b3
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

Loading…