Sodium borohydride → HCID 13911618, Verbindung

HRID 653464

Reaktionsgleichung

Reaktionsgleichung von HRID 653464
[S:1]1[C:5]2[S:6](=[O:11])(=[O:10])[CH2:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[S:12]([NH2:15])(=[O:14])=[O:13].[OH2:16].Cl([O-])(=O)=[O:18].[Ba+2].Cl([O-])(=O)=O.[BH4-].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[OH:16][CH:9]1[CH:8]([OH:18])[CH2:7][S:6](=[O:10])(=[O:11])[C:5]2[S:1][C:2]([S:12]([NH2:15])(=[O:13])=[O:14])=[CH:3][C:4]1=2

Komponenten

7

Edukt 3

HCID 4311764Sodium borohydrideHCID 6096944Chloric acid, barium salt, monohydrateHCID 137631516H-Thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

Produkt 1

HCID 13911618HCID 13911618, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A solution of 6H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide (1.15 g, 0.0043 m) in tetrahydrofuran (20 ml) was added to a stirred solution of barium chlorate monohydrate (2.23 g, 0.0069 m) in water (20 ml) under a nitrogen atmosphere. Osmium tetroxide (0.66 g, 0.0026 m) was added and the mixture was stirred at 45° C. for 22 hours. Sodium borohydride (0.16 g, 0.0043 m) was added portionwise and the mixture was stirred at ambient temperature for one hour. After filtering through "Super-Cel", the filtrate was concentrated under reduced pressure at 30° C. to remove tetrahydrofuran, the aqueous suspension was acidified with 6N hydrochloric acid (1.0 ml) and extracted with ethyl acetate (3×75 ml). The combined extracts were washed twice with water, dried over sodium sulfate and concentrated in vacuo to yield 0.81 g (63% yield) of crude product which was purified by chromatography on silica gel, eluting with 15% methanol-chloroform. Recrystallization from nitromethane afforded an analytical sample melting at 182.5°-185° C.

Aufarbeitung

  1. stirringthe mixture was stirred at ambient temperature for one hour
  2. filtrationAfter filtering through "Super-Cel"
  3. concentrationthe filtrate was concentrated under reduced pressure at 30° C.
  4. customto remove tetrahydrofuran
  5. extractionextracted with ethyl acetate (3×75 ml)
  6. washThe combined extracts were washed twice with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-419cdc8b03434c2d9b307bca9086a8ac
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04677115

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