Phenylacetaldehyde → HCID 19016751, compound

Reaction equation

[N+]([O-])(O)=O.[N+:5]([O-])(O)=O.[C:9]([OH:18])(=O)[CH:10]([CH:12]([C:14]([OH:16])=[O:15])O)O.[C:19]1([CH2:25][CH:26]=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)=O.CC(C)=O.[OH-:35].[NH4+:36]>>[CH2:25]([C:26]1[NH:36][C:12]([C:14]([OH:16])=[O:15])=[C:10]([C:9]([OH:18])=[O:35])[N:5]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Reactant 4

HCID 998Phenylacetaldehyde2×

HCID 14923Ammonium Hydroxide3×

HCID 18522661Acetone cardice

HCID 86747982HCID 86747982, compound

Product 1

HCID 19016751HCID 19016751, compound

Procedure

Tartaric acid dinitrate (0.67 mol) was neutralized to congo red test paper with concentrated ammonium hydroxide (500 mL). Additional concentrated ammonium hydroxide (50 mL) was added followed by a phenylacetaldehyde solution [previously prepared by the careful addition of phenylacetaldehyde (3.5 mol) to concentrated ammonium hydroxide (250 mL) with ice bath cooling]. The dry ice-acetone bath was replaced with ice-water and the reaction mixture was allowed to warm to room temperature over 16 hours. The precipitate was filtered, resuspended in water (400 mL) and stirred, filtered and the solid was washed with water (3×75 mL), methanol (2×40 mL) and ether (2×40 mL), then dried under vacuum to give 2-benzyl-4,5-imidazoledicarboxylic acid.