Acetic Anhydride → HCID 18544122, compound

HRID 1268113Notes

Reaction equation

HRID 1268113 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[N+:8]([C:11]1[CH:37]=[CH:36][C:14]([CH2:15][O:16][C:17]2[CH:18]=[C:19]([CH:33]=[CH:34][CH:35]=2)[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29](=[O:32])(=[O:31])[NH2:30])=[O:21])=[CH:13][CH:12]=1)([O-:10])=[O:9]>CN(C)C1C=CN=CC=1.O1CCCC1>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([CH2:15][O:16][C:17]2[CH:18]=[C:19]([CH:33]=[CH:34][CH:35]=2)[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([NH:30][C:1](=[O:3])[CH3:2])(=[O:32])=[O:31])=[O:21])=[CH:36][CH:37]=1)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 12041317HCID 12041317, compound

Product 1

HCID 18544122HCID 18544122, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and at 0° C. 0.07 ml (0.80 mmol) of acetic anhydride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 300 mg (0.70 mol) of 3-(4-nitrobenzyloxy)-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 5 and 171 mg (1.40 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 purified by a silica gel column chromatography to obtain 290 mg (yield: 89.8%) of the title compound.

Workup

  1. customat 0° C
  2. customthe solvent was evaporated under a reduced pressure
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materiala potassium hydrgensulfate aqueous solution and saturated brine in that order and dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-7f04d6ab30194c5496cb088051452e7b
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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