Nitric Acid → 3-(2,2-dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester

HRID 5772Notes

Reaction equation

HRID 5772 reaction equation
N([O-])=O.[Na+].[N+]([O-])(O)=O.[CH3:9][O:10][C:11]([C:13]1[N:17]([CH:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][C:19]2([CH3:28])[CH3:27])[C:16](S)=[N:15][CH:14]=1)=[O:12].[OH-].[Na+]>O>[CH3:9][O:10][C:11]([C:13]1[N:17]([CH:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][C:19]2([CH3:28])[CH3:27])[CH:16]=[N:15][CH:14]=1)=[O:12]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178418612HCID 178418612, compound

Product 1

HCID 218730963-(2,2-dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl esterYield 96.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g of sodium nitrite and 17.4 ml of nitric acid are solved in 140 ml of deionisized water. Within 20 min. 28 g of 1-(2,2-dimethyl-indan-1-yl)-2-mercapto-5-imidazolecarboxylic acid methyl ester are added portionwise at a temperature between 30° C. and 50° C. The reaction mixture is treated with conc. aqueous sodium hydroxide solution. Extracting the aqueous phase with chloroform, and evaporating the organic solvent yields 24.2 g of 1-(2,2-dimethyl-indan-1-yl)-5-imidazolecarboxylic acid methyl ester as a colourless product (m.p. 96°-97° C.).

Workup

  1. extractionExtracting the aqueous phase with chloroform
  2. customevaporating the organic solvent

Sources & evidence

ORD record
ord-13f80b85ece745a599e02367384e39e8
Source dataset
uspto-grants-1993_09
Patent number
US05246915

Reaction notes

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