1-Propanethiol, 2-amino- → 3(R,S)-methyl-7-sulfamoyl-3,4-dihydrothieno[3,2-f]-1,4-thiazepin-5(2H)-one

HRID 1197431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1197431
CC(C)([O-])C.[K+].[NH2:7][CH:8]([CH3:11])[CH2:9][SH:10].Cl[C:13]1[S:14][C:15]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:16][C:17]=1[C:18](OCC)=[O:19]>C(O)C>[CH3:11][CH:8]1[NH:7][C:18](=[O:19])[C:17]2[CH:16]=[C:15]([S:23](=[O:25])(=[O:26])[NH2:24])[S:14][C:13]=2[S:10][CH2:9]1

Komponenten

5

Edukt 3

HCID 1658451-Propanethiol, 2-amino-HCID 19106450Ethyl 2-chloro-5-sulfamoylthiophene-3-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 191064643(R,S)-methyl-7-sulfamoyl-3,4-dihydrothieno[3,2-f]-1,4-thiazepin-5(2H)-oneAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a mixture of potassium tert-butoxide (8.56 g, 0.076 mol) in ethanol (75 mL) was added 2(R,S)-aminopropanethiol (3.1 g, 0.0246 mol) and ethyl 2-chloro-5-sulfamoylthiophene-3-carboxylate (5.98 g, 0.022 mol). The mixture was heated at reflux for 24 hours, and then allowed to stand at room temperature for 24 hours. Following removal of most of the solvent by vacuum concentration, the mixture was acidified to pH 3 with dilute hydrochloric acid. The resulting solids were removed by filtration and dried to give 4.44 g of the title compound, mp 184°-187° C.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hours
  3. customremoval of most of the solvent
  4. concentrationby vacuum concentration
  5. customThe resulting solids were removed by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-010f263d5e2e4fe6933dd53dea498f88
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05276025

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