Carbon Disulfide → 2-Thioadenosine

HRID 1729619Notes

Reaction equation

HRID 1729619 reaction equation
C(O[N:4]=[C:5]([C:7]1[N:8]=[CH:9][N:10]([C@@H:13]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@H:14]2[OH:15])[C:11]=1[NH2:12])[NH2:6])C.[C:22](=S)=[S:23]>N1C=CC=CC=1.CO>[CH:9]1[N:10]([C@@H:13]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@H:14]2[OH:15])[C:11]2[C:7](=[C:5]([NH2:6])[NH:4][C:22]([N:12]=2)=[S:23])[N:8]=1

Participants

5

Reactant 2

HCID 6348Carbon DisulfideHCID 537630935-amino-1-beta-D-ribofuranosylimidazole-4-carboxamide O-ethyl-oxime

Product 1

HCID 64519652-ThioadenosineYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

0.45 g of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide O-ethyl-oxime was dissolved in a mixture of 0.3 ml of pyridine, 5 ml of methanol and 0.5 ml of carbon disulfide. The resulting mixture was allowed to react in an autoclave at 120° C for 6 hours under autogenous pressure (about 10 Kg/cm2). The reaction mixture was concentrated to dryness, and the residue was dissolved in water. The aqueous solution was adjusted to a pH of 2 with hydrochloric acid to precipitate the crude product, which was then recovered by filtration. The filter cake was dissolved in aqueous ammonia, the solution was filtered, and the filtrate was adjusted to a pH of 2 with hydrochloric acid to obtain 0.31 g of pure 2-thioadenosine as crystals having a melting point of 199° C (with decomposition) in a 65% yield.

Workup

  1. customto react in an autoclave at 120° C for 6 hours under autogenous pressure (about 10 Kg/cm2)
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in water
  4. customto precipitate the crude product, which
  5. filtrationwas then recovered by filtration
  6. dissolutionThe filter cake was dissolved in aqueous ammonia
  7. filtrationthe solution was filtered

Sources & evidence

ORD record
ord-3467b6f4200a42b78448af9d64e5a7af
Source dataset
uspto-grants-1976_11
Patent number
US03989682

Reaction notes

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