Carbon Disulfide → 2-Thioadenosine

HRID 1729614Notes

Reaction equation

HRID 1729614 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:28](=S)=[S:29]>[OH-].[Na+].CO.N>[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:28]([N:16]=2)=[S:29])[N:12]=1

Participants

6

Reactant 2

HCID 6348Carbon DisulfideHCID 53795338HCID 53795338, compound

Product 1

HCID 64519652-ThioadenosineYield 72%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

0.45 g of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide O-(p-methylbenzyl)-oxime was dissolved in a mixture of 0.30g of sodium hydroxide, 5 ml of methanol and 0.5 ml of carbon disulfide, and the resulting mixture was allowed to react in an autoclave at 130° C for 4 hours under autogenous pressure (about 10 Kg/cm2). The reaction mixture was concentrated to dryness, and the residue was dissolved in water. The resulting aqueous solution was adjusted to a pH of 2 with hydrochloric acid, and the precipitated crystals were filtered to obtain crude 2-thioadenosine. The crude product was dissolved in aqueous ammonia, filtered and adjusted to a pH of 2 with hydrochloric acid to obtain 0.27 g of pure 2-thioadenosine having a melting point of 198° C (with decomposition) in a 72% yield.

Workup

  1. customto react in an autoclave at 130° C for 4 hours under autogenous pressure (about 10 Kg/cm2)
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in water
  4. filtrationthe precipitated crystals were filtered
  5. customto obtain crude 2-thioadenosine
  6. filtrationfiltered

Sources & evidence

ORD record
ord-afdd774bfea849fd9e1601a674a7bb2a
Source dataset
uspto-grants-1976_11
Patent number
US03989682

Reaction notes

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