2-Aminothiazole → 4-Acetyl-n-(thiazol-2-yl)benzenesulfonamide

HRID 1434681Notes

Reaction equation

HRID 1434681 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[NH2:14][C:15]1[S:16][CH:17]=[CH:18][N:19]=1>ClCCl.N1C=CC=CC=1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 21552-AminothiazoleHCID 2664184-Acetylbenzenesulfonyl chloride

Product 1

HCID 210825294-Acetyl-n-(thiazol-2-yl)benzenesulfonamideYield 70%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-acetyl-benzenesulfonyl chloride (50 mmol) and 2-aminothiazole (50 mmol) in dichloromethane and pyridine (300 mL, 8:2) was stirred for one day. After concentrated in vacuo, the residue was diluted with ethyl acetate (500 mL) and the solution was washed with 1N HCl solution, sat NaHCO3, dried over MgSO4, and concentrated in vacuo. The residue was recrystallized in ethyl acetate to give 4-acetyl-N-thiazol-2-yl-benzenesulfonamide (35 mmol) as a yellow solid.

Workup

  1. concentrationAfter concentrated in vacuo
  2. additionthe residue was diluted with ethyl acetate (500 mL)
  3. washthe solution was washed with 1N HCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-c6d290bbaf614ea19e21631e3c9af60c
Source dataset
uspto-grants-2009_11
Patent number
US07615569B2

Reaction notes

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