1,8-Diazabicyclo(5.4.0)undec-7-ene → 4,5-Dihydro-2-(2-sulfamoylphenylmethylthio)thiazole

HRID 1762718

Reaktionsgleichung

Reaktionsgleichung von HRID 1762718
N12CCCN=C1CCCCC2.[SH:12][C:13]1[S:14][CH2:15][CH2:16][N:17]=1.Cl[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26]([NH2:29])(=[O:28])=[O:27]>C(#N)C.O>[S:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][S:12][C:13]1[S:14][CH2:15][CH2:16][N:17]=1)(=[O:27])(=[O:28])[NH2:29]

Komponenten

6

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 133646272-(Chloromethyl)benzenesulfonamideHCID 178527880HCID 178527880, Verbindung

Produkt 1

HCID 200417444,5-Dihydro-2-(2-sulfamoylphenylmethylthio)thiazoleAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

With cooling, 7.9 g of 97% 1,8-diazabicyclo[5.4.0]undec-7-ene are added to a suspension of 6.2 g of 97% 4,5-dihydro-2-mercaptothiazole in 50 ml of acetonitrile. To the yellow solution so obtained are added 10.3 g of 2-chloromethylbenzenesulfonamide and the reaction mixture is stirred for 1 hour at 20°-25° C. The reaction solution is then diluted with about 1 liter of water. The precipitate is isolated by filtration and dried, affording 11.9 g (76% of theory) of 4,5-dihydro-2-(2-sulfamoylphenylmethylthio)thiazole of m.p. 123°-125° C.

Aufarbeitung

  1. temperatureWith cooling
  2. customTo the yellow solution so obtained
  3. customThe precipitate is isolated by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d1595ff3a773421eba2f8c639abf8351
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04833252

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