Sodium Hydroxide → 5-Ethynyl-1H-imidazole-4-carboxamide

HRID 345757Notes

Reaction equation

HRID 345757 reaction equation
[C:1]([C:3]1[N:7]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[CH:6]=[N:5][C:4]=1[C:17]([NH2:19])=[O:18])#[CH:2].[OH-].[Na+]>Cl>[C:1]([C:3]1[NH:7][CH:6]=[N:5][C:4]=1[C:17]([NH2:19])=[O:18])#[CH:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4531805-Ethynyl-1-pentofuranosyl-1H-imidazole-4-carboximidic acid

Product 1

HCID 148868435-Ethynyl-1H-imidazole-4-carboxamideYield 37.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 200 mg (0.75 mmol) of 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide in 5 ml of 1N hydrochloric acid solution was heated under reflux at 100° C. for 4 hours. After the reaction, the reaction solution was neutralized with lN sodium hydroxide solution, silica gel powder was added, and the solvent was evaporated. The residue was adsorbed onto a silica gel column (2.7×11 cm), eluted with a 0-16% ethanol-chloroform solvent mixture, and crystallized from an ethanol-hexane solvent mixture to obtain 38 mg of pale yellow crystals of 5-ethynylimidazole-4-carboxamide (yield: 37.6%).

Workup

  1. customAfter the reaction
  2. additionwas added
  3. customthe solvent was evaporated
  4. washeluted with a 0-16% ethanol-chloroform solvent mixture
  5. customcrystallized from an ethanol-hexane solvent mixture

Sources & evidence

ORD record
ord-76fa2f4404f74a189199459ee246849b
Source dataset
uspto-grants-1991_10
Patent number
US05059590

Reaction notes

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