Acetyl chloride → N-(2-Sulfamoylphenyl)acetamide

HRID 1767670Notes

Reaction equation

HRID 1767670 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].C(N(CC)CC)C.[C:19](Cl)([CH3:21])=[O:20]>C1COCC1>[C:19]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:9])=[O:10])(=[O:20])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 728942-Aminobenzenesulfonamide

Product 1

HCID 12489724N-(2-Sulfamoylphenyl)acetamideYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2-aminobenzenesulfonamide (1.72 g; 10 mmol) and triethylamine (1.53 ml; 11 mmol) in THF (25 ml) at 0° C. was added AcCl (0.85 ml; 12 mmol) and left with stirring at rt. over night. The reaction mixture was filtered and adsorbed onto silica. Column chromatography gave 1.7 g (79%) product. M.p. 153.5–155.5° C.

Workup

  1. waitleft
  2. waitover night
  3. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-14ab805bd29d4be492cf6383b98004eb
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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