Ethanol → 2-Thioadenosine

HRID 1729612Notes

Reaction equation

HRID 1729612 reaction equation
CC1C=CC(CO[N:8]=[C:9]([C:11]2[N:12]=[CH:13][N:14]([C@@H:17]3[O:23][C@H:22]([CH2:24][OH:25])[C@@H:20]([OH:21])[C@H:18]3[OH:19])[C:15]=2[NH2:16])[NH2:10])=CC=1.C(O)C.[C:31](=S)=[S:32]>>[CH:13]1[N:14]([C@@H:17]2[O:23][C@H:22]([CH2:24][OH:25])[C@@H:20]([OH:21])[C@H:18]2[OH:19])[C:15]2[C:11](=[C:9]([NH2:10])[NH:8][C:31]([N:16]=2)=[S:32])[N:12]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6348Carbon DisulfideHCID 53795338HCID 53795338, compound

Product 1

HCID 64519652-ThioadenosineYield 76%

Procedure

0.45 g of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide O-(p-methylbenzyl)-oxime was dissolved in 8 ml of an aqueous solution containing 1 ml of ethanol, and 2 ml of carbon disulfide was added to the solution. The resulting mixture was allowed to react in an autoclave at 130° C for 5 hours under autogenous pressure (about 10 Kg/cm2), and the reaction product was worked up in the same manner as described in Example 1 to obtain 0.288 g of 2-thioadenosine having a melting point of 198° C (with decomposition) in a 76% yield.

Workup

  1. additionwas added to the solution
  2. customto react in an autoclave at 130° C for 5 hours under autogenous pressure (about 10 Kg/cm2)

Sources & evidence

ORD record
ord-85f2ecd6fb614c7faf0d3ad7f6fea081
Source dataset
uspto-grants-1976_11
Patent number
US03989682

Reaction notes

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