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

HRID 559501Notes

Reaction equation

HRID 559501 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-130978aa94e344abb751a468a34eae30
Source dataset
uspto-grants-2011_11
Patent number
US08063080B2

Reaction notes

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