Reaktion #1005010

Reaktionsgleichung

hydrogen sulfide

Hydrogen sulfide

7

4-cyano-2-(2,3,5-tri-O-acetyl-β -D-ribofuranosyl)-1,2,3-triazole

triethylamine

→

9

Ausbeute 98.0%

2-(2,3,5-Tri-O-acetyl-β -D-ribofuranosyl)-1,2,3-triazole-4-thiocarboxamide

Ausbeute 98.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONhad been added
2. 2
   Sonstigethe solvent was removed
3. 3
   workup.DISSOLUTIONThe resultant syrup was dissolved in a minimum of chloroform
4. 4
   workup.ADDITIONadded to a silica gel column (2 × 38 cm)
5. 5
   WaschenThe column was eluted with chloroform (0.25 liter) and chloroform-ethyl acetate (9:1, 0.5 liter)
6. 6
   Sonstige20 ml fractions were collected

Vorschrift

Hydrogen sulfide was passed through a suspension of 2.0 g of 7 in ethanol (60 ml) to which 3.5 ml of triethylamine had been added. After 2 1/2 hr passage of hydrogen sulfide was ceased and the solvent was removed. The resultant syrup was dissolved in a minimum of chloroform and added to a silica gel column (2 × 38 cm) packed in chloroform. The column was eluted with chloroform (0.25 liter) and chloroform-ethyl acetate (9:1, 0.5 liter); 20 ml fractions were collected. Fractions 19-34 provided 2.6 g (98%) of 9 as a syrup; nmr (DMSO-d6) δ 6.36 (d, 1, J1',2' 2.0 Hz, 1'--H), 8.39 (s, 1,5--H); (CDCl3) δ 6.24 (d, 1, J1'2' 3.0 Hz, 1'--H), 8.32 (s, 1, 5--H).

Quelle