Carbon Disulfide → 2-Thioadenosine

HRID 1729620Notes

Reaction equation

HRID 1729620 reaction equation
C1(O[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])CCCCC1.[C:26](=S)=[S:27]>C(N(CC)CC)C.CN(C)C=O>[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:26]([N:16]=2)=[S:27])[N:12]=1

Participants

5

Reactant 2

HCID 6348Carbon DisulfideHCID 542910965-amino-1-beta-D-ribofuranosylimidazole-4-carboxamide O-cyclohexyl-oxime

Product 1

HCID 64519652-ThioadenosineYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

0.45 g of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide O-cyclohexyl-oxime was dissolved in a mixture of 0.2 ml of triethylamine and 5 ml of N,N-dimethylformamide, and 0.5 ml of carbon disulfide was further added to the solution. The resulting mixture was allowed to react in an autoclave at 125° C for 5 hours under autogenous pressure (about 10 Kg/cm2) followed by working up in the same manner as described in Example 15 to obtain 0.26 g (yield, 65%) of 2-thioadenosine having a melting point of 197° C (with decomposition).

Workup

  1. additionwas further added to the solution
  2. customto react in an autoclave at 125° C for 5 hours under autogenous pressure (about 10 Kg/cm2)

Sources & evidence

ORD record
ord-d7de27e4cdc44a67b21a62a41adacfa7
Source dataset
uspto-grants-1976_11
Patent number
US03989682

Reaction notes

Loading…