Acetic Anhydride → N-[2-(4-Phenylethynylbenzamido)benzenesulfonyl]acetamide

HRID 1268132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1268132
C(O[C:5](=[O:7])[CH3:6])(=O)C.[C:8]1([C:14]#[C:15][C:16]2[CH:34]=[CH:33][C:19]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29](=[O:32])(=[O:31])[NH2:30])=[O:21])=[CH:18][CH:17]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C)C1C=CN=CC=1.O1CCCC1>[C:8]1([C:14]#[C:15][C:16]2[CH:34]=[CH:33][C:19]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29]([NH:30][C:5](=[O:7])[CH3:6])(=[O:31])=[O:32])=[O:21])=[CH:18][CH:17]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 2

HCID 7918Acetic AnhydrideHCID 120430434-Phenylethynyl-N-(2-sulfamoylphenyl)benzamide

Produkt 1

HCID 59057402N-[2-(4-Phenylethynylbenzamido)benzenesulfonyl]acetamideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a stream of nitrogen and at 0° C., 0.15 ml (1.60 mmol) of acetic anhydride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 500 mg (1.30 mmol) of 4-phenylethynyl-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 10 and 320 mg (2.60 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 methanol to obtain 430 mg (yield: 77.6%) of the title compound.

Aufarbeitung

  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 methanol

Quellen und Nachweise

ORD-Eintrag
ord-1d90a2674f8041d38dca4d7271d7b1ce
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06555584B1

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