Ammonium Chloride → Taribavirin Hydrochloride

HRID 1703733Notes

Reaction equation

HRID 1703733 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].[Cl-:26].[NH4+:27]>N>[ClH:26].[C@@H:8]1([N:5]2[CH:6]=[N:7][C:3]([C:1]([NH2:2])=[NH:27])=[N:4]2)[O:20][C@H:19]([CH2:21][OH:22])[C@@H:14]([OH:15])[C@H:9]1[OH:10]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 134568011-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carbonitrile

Product 1

HCID 451447Taribavirin Hydrochloride

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A mixture of 3-cyano-1-(2,3,5-tri-O-acetyl-β -D-ribofuranosyl)-1,2,4-triazole (7.04 g., 20.0 mmole) ammonium chloride (1.07 g., 20.0 mmol) and anhydrous ammonia (150 ml.) was heated in a bomb at 85° for 18 hours. After removal of excess ammonia, the residue was crystallized from acetonitrile-ethanol to provide 5.30 g. (95%) of product with M.P. 177°-179° dec.

Workup

  1. temperaturewas heated in a bomb at 85° for 18 hours
  2. customAfter removal of excess ammonia
  3. customthe residue was crystallized from acetonitrile-ethanol
  4. customto provide 5.30 g

Sources & evidence

ORD record
ord-9203cc9c20d445de9ecdcc8ad0a34a8c
Source dataset
uspto-grants-1978_11
Patent number
USRE029835

Reaction notes

Loading…