Acetic Anhydride → N-[2-[3-(4-Chlorobenzyloxy)benzamido]benzenesulfonyl]acetamide

HRID 1268109Notes

Reaction equation

HRID 1268109 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:35]=[CH:34][C:12]([CH2:13][O:14][C:15]2[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=2)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[S:27](=[O:30])(=[O:29])[NH2:28])=[O:19])=[CH:11][CH:10]=1>CN(C)C1C=CN=CC=1.O1CCCC1>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][O:14][C:15]2[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=2)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[S:27]([NH:28][C:1](=[O:3])[CH3:2])(=[O:30])=[O:29])=[O:19])=[CH:34][CH:35]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 120413153-(4-Chlorobenzyloxy)-N-(2-sulfamoylphenyl)benzamide

Product 1

HCID 18544080N-[2-[3-(4-Chlorobenzyloxy)benzamido]benzenesulfonyl]acetamideYield 52.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and at 0° C., 0.12 ml (1.30 mmol) of acetic anhydride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 500 mg (1.20 mmol) of 3-(4-chlorobenzyloxy)-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 4 and 293 mg (2.40 mmol) of 4-dimethylaminopyridine, the mixture was stirred at room temperature for 1 hour and then the solvent was evaporated under a reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with water, a potassium hydrgensulfate aqueous solution and saturated brine in that order and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The resulting residue was recrystallized from an ethyl acetate-diethyl ether mixed solvent to obtain 290 mg (yield: 52.7%) of the title compound.

Workup

  1. customthe solvent was evaporated under a reduced pressure
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materiala potassium hydrgensulfate aqueous solution and saturated brine in that order and dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe resulting residue was recrystallized from an ethyl acetate-diethyl ether mixed solvent

Sources & evidence

ORD record
ord-70071fae955146d4b4ea3384ca24958b
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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