Hydrochloric Acid → 5(R,S)-methyl-7-sulfamoyl-2,3,4,5-tetrahydrothieno [3,2-f]-1,4-thiazepine

HRID 1197436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1197436
[Na].[SH:2][CH2:3][CH2:4][NH2:5].[C:6]([C:9]1[CH:10]=[C:11]([S:15]([NH2:18])(=[O:17])=[O:16])[S:12][C:13]=1Cl)(=O)[CH3:7].[BH4-].[Na+].Cl>C(O)C>[CH3:7][CH:6]1[C:9]2[CH:10]=[C:11]([S:15](=[O:17])(=[O:16])[NH2:18])[S:12][C:13]=2[S:2][CH2:3][CH2:4][NH:5]1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 6058CysteamineHCID 4311764Sodium borohydrideHCID 5360545SodiumHCID 191064694-Acetyl-5-chlorothiophene-2-sulfonamide

Produkt 1

HCID 571467665(R,S)-methyl-7-sulfamoyl-2,3,4,5-tetrahydrothieno [3,2-f]-1,4-thiazepineAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Sodium metal (0.46 g, 0.02 mol) was dissolved in absolute ethanol (50 mL), under a nitrogen atmosphere and 2-mercaptoethylamine (1.55 g, 0.02 mol) was added. After 10 minutes, 4-acetyl-5-chlorothiophene-2-sulfonamide (1.63 g, 0.007 mol) in dry ethanol (70 mL) was added to the reaction and the mixture refluxed for 18 hours. The reaction was cooled to room temperature and sodium borohydride (1.0 g, 0.026 mol) was added. After three hours the reaction mixture was poured into ice water and acidified with 6N HCl. The aqueous solution was extracted with ethyl acetate and the aqueous solution made basic with NaHCO3 and Na2CO3. The product was extracted into ethyl acetate, the extract was dried (Na2SO4), filtered and evaporated. The residue (1.77 g) was crystallized from ethyl acetate-methanol to give analytically pure product (1.58 g, 85%), mp 182°-185° C.

Aufarbeitung

  1. temperaturethe mixture refluxed for 18 hours
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. extractionThe product was extracted into ethyl acetate
  4. dry with materialthe extract was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue (1.77 g) was crystallized from ethyl acetate-methanol

Quellen und Nachweise

ORD-Eintrag
ord-0d68743f52f3493f950331fa6f3fb04d
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05276025

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