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Acetic Acid → 1-(beta-D-ribofuranosyl)-5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamide

HRID 1588946
Notes
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Reaction equation

HRID 1588946 reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[CH:5]=[N:4][C:3]=1[C:16]([NH2:18])=[O:17].C([N:27]=[C:28]=[S:29])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CN(C=O)C.O.CO>[C@@H:7]1([N:6]2[C:2]([NH:1][C:28](=[S:29])[NH2:27])=[C:3]([C:16]([NH2:18])=[O:17])[N:4]=[CH:5]2)[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]1[OH:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 17513AcadesineHCID 68284Benzoyl isothiocyanate

Product 1

HCID 537754951-(beta-D-ribofuranosyl)-5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamideYield 81.4%

Reagents, catalysts & solvents 3

HCID 887
Methanol
Solvent
HCID 962WaterSolvent2×
HCID 6228DimethylformamideSolvent

Procedure

5-Amino-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxamide (5.0 g, 19.4 mM) and benzoylisothiocyanate (3.3 g, 20 mM) was stirred at room temperature in DMF (40 ml) for 1 hour. The solvent was stripped off in water-jet vacuo. The residue was dissolved in methanol (160 ml) and potassium carbonate (1.6 g, 11.6 mM) in water (8 ml) was added whereafter the mixture was refluxed at 2 hours. After cooling to room temperature acetic acid was added to pH 6. The reaction mixture was evaporated in water-jet vacuo, and the residue was crystallized from ethanol. Hereby was isolated 5.0 g of crude 1-(β-D-ribofuranosyl)-5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamide. HPLC indicated a purity of about 65% (the remaining 35% was essentially potassium acetate).

Workup

  1. temperaturewas refluxed at 2 hours
  2. additionwas added to pH 6
  3. customThe reaction mixture was evaporated in water-jet vacuo
  4. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-3f701f34da3f4a0397ea5d11b98f7352
Source dataset
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05223619

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes