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

HRID 1268123
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1268123
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([C:12]1[CH:38]=[CH:37][C:15]([CH2:16][O:17][C:18]2[CH:19]=[C:20]([CH:34]=[CH:35][CH:36]=2)[C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30](=[O:33])(=[O:32])[NH2:31])=[O:22])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9]>CN(C)C1C=CN=CC=1.O1CCCC1>[C:8]([C:12]1[CH:38]=[CH:37][C:15]([CH2:16][O:17][C:18]2[CH:19]=[C:20]([CH:34]=[CH:35][CH:36]=2)[C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30]([NH:31][C:1](=[O:3])[CH3:2])(=[O:33])=[O:32])=[O:22])=[CH:14][CH:13]=1)([CH3:11])([CH3:9])[CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 7918Acetic AnhydrideHCID 120413093-(4-t-Butylbenzyloxy)-N-(2-sulfamoylphenyl)benzamide

Produkt 1

HCID 18544150N-[2-[3-(4-t-Butylbenzyloxy)benzamido]benzenesulfonyl]acetamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

In a stream of nitrogen and at 0° C., 0.11 ml (1.10 mmol) of acetic anhydride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 438 mg (1.00 mmol) of 3-(4-t-butylbenzyloxy)-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 2 and 249 mg (2.00 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 456 mg (yield: 96.0%) 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 purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a72975e3f8ed40448f0876351dd64398
Quelldatensatz
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06555584B1

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