Acetic Acid → 4-Acetoxy-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

HRID 653461

Reaktionsgleichung

Reaktionsgleichung von HRID 653461
[OH:1][CH:2]1[CH2:7][CH2:6][S:5](=[O:9])(=[O:8])[C:4]2[S:10][C:11]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:12][C:3]1=2.[C:17](O)(=[O:19])[CH3:18].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.O1CCCC1>[C:17]([O:1][CH:2]1[CH2:7][CH2:6][S:5](=[O:9])(=[O:8])[C:4]2[S:10][C:11]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:12][C:3]1=2)(=[O:19])[CH3:18]

Komponenten

6

Edukt 3

HCID 176Acetic Acid2×HCID 10868DicyclohexylcarbodiimideHCID 136170125,6-Dihydro-4-hydroxy-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide

Produkt 1

HCID 139116164-Acetoxy-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxideAusbeute 111,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5,6-Dihydro-4-hydroxy-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide (2.00 g, 0.0071 m), glacial acetic acid (0.92 g, 0.015 m) and 4-dimethylaminopyridine (0.085 g, 0.0007 m) were dissolved in dry tetrahydrofuran (30 ml) and the solution was cooled to 0° C. under nitrogen and stirred while a solution of dicyclohexylcarbodiimide (1.61 g, 0.0078 m) in dry tetrahydrofuran (10 ml) was added over 10 minutes. After stirring at 0° C. for 1 hour and at ambient temperature for 2 hours, an additional 0.46 g (0.0077 m) of glacial acetic acid was added and stirring was continued at ambient temperature for one hour more. The mixture was filtered and the solid was washed with tetrahydrofuran. The combined filtrate and washings were evaporated in vacuo to give a quantitative yield (2.31 g) of crude product. This material was combined with 1.14 g of identical product from a previous run and chromatographed on silica gel, eluting with 10% methanol-chloroform, to yield 2.57 g (75%) of product. Recrystallization from nitromethane afforded an analytical sample melting at 187.5°-188.5° C.

Aufarbeitung

  1. additionwas added over 10 minutes
  2. stirringstirring
  3. waitwas continued at ambient temperature for one hour
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with tetrahydrofuran
  6. customThe combined filtrate and washings were evaporated in vacuo
  7. customto give a quantitative yield (2.31 g) of crude product
  8. customchromatographed on silica gel
  9. washeluting with 10% methanol-chloroform

Quellen und Nachweise

ORD-Eintrag
ord-e830d25dbf524e4abb54c33de19f2f6b
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04677115

Verknüpfte Notizen

Wird geladen…