Water → 5-(benzenesulfonyl)-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole

HRID 902872

Reaktionsgleichung

Reaktionsgleichung von HRID 902872
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:12][C:13]1[N:14]=[CH:15][S:16][C:17]=1[CH2:18]Br.[H-].[Na+].O>CN(C)C=O.C(Cl)Cl>[C:1]1([S:7]([N:10]2[CH2:18][C:17]3[S:16][CH:15]=[N:14][C:13]=3[CH2:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7370BenzenesulfonamideHCID 24758Sodium hydrideHCID 108496984,5-Bis(bromomethyl)thiazole

Produkt 1

HCID 184428065-(benzenesulfonyl)-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzenesulfonamide (638 mg) and 4,5-bis(bromomethyl)thiazole (M. Al. Hariri, O. Galley, F. Pautet, H. Fillion, Eur. J. Org. Chem., 1998, 593-594.) (1.10 g) were dissolved in N,N-dimethylformamide (10 ml), sodium hydride (60% in oil, 357 mg) was added at a time, and the mixture was stirred at room temperature for 3 hours. Water and methylene chloride were added to conduct liquid separation. After the resultant organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by column chromatography on silica gel (methylene chloride:ethyl acetate=9:1) to obtain the title compound (137 mg).

Aufarbeitung

  1. customliquid separation
  2. dry with materialAfter the resultant organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off
  4. customthe residue was purified by column chromatography on silica gel (methylene chloride:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-39e55d46c1b1468caadb96261d27420d
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365205B2

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