Hydrogen Sulfide → 1-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-[1,2,4]triazole-3-carbothioic acid amide

HRID 1703731Notes

Reaction equation

HRID 1703731 reaction equation
[C:1]([C:3]1[N:7]=[CH:6][N:5]([C@@H:8]2[O:20][C@H:19]([CH2:21][O:22]C(=O)C)[C@@H:14]([O:15]C(=O)C)[C@H:9]2[O:10]C(=O)C)[N:4]=1)#[N:2].C(N(CC)CC)C.S.C(N)=[S:35]>C(O)C>[C@@H:8]1([N:5]2[CH:6]=[N:7][C:3]([C:1](=[S:35])[NH2:2])=[N:4]2)[O:20][C@H:19]([CH2:21][OH:22])[C@@H:14]([OH:15])[C@H:9]1[OH:10]

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 3005587MethanethioamideHCID 134568011-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carbonitrile

Product 1

HCID 30070661-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-[1,2,4]triazole-3-carbothioic acid amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-cyano-1-(2,3,5-tri-O-acetyl-β -D-ribofuranosyl)-1,2,4-triazole (8.0 g., 22.7 mmole), triethylamine (14.0 ml.) and ethanol (200 ml.) was stirred at 25° while hydrogen sulfide gas was passed into the solution for 2 hrs. The solvent was removed and the residue was treated with a solution of sodium methoxide (600 mg.) in methanol (150 ml.) for three hours at 25°. After the solution was neutralized with Bio-Rad AG 50W-X2(H), it as filtered, and the solvent was removed. Crystallization of the product from aqueous ethanol provided 4.5 g. (76.0%) of the thiocarboxamide with M.P. 173-175°.

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with a solution of sodium methoxide (600 mg.) in methanol (150 ml.) for three hours at 25°
  3. filtrationit as filtered
  4. customthe solvent was removed
  5. customCrystallization of the product from aqueous ethanol
  6. customprovided 4.5 g

Sources & evidence

ORD record
ord-746d2f1bb4bc43b7bc11167e372c937f
Source dataset
uspto-grants-1978_11
Patent number
USRE029835

Reaction notes

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