Nitric Acid → 1-Benzyl-5-hydroxymethyl-1H-imidazole

HRID 1380990

Reaction equation

HRID 1380990 reaction equation
[CH2:1]([N:8]1[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[C:9]1S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([O-])(O)=O.[OH-].[Na+]>O>[CH2:1]([N:8]1[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 1785198455-Hydroxymethyl-2-mercapto-1-benzylimidazole

Product 1

HCID 27732351-Benzyl-5-hydroxymethyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Benzyl-2-mercapto-5-hydroxymethyl-imidazole (7.5 g) is added in small portions to a mixture of water (18 ml) and concentrated nitric acid (7.5 g) at 35° C. The mixture is stirred for 3 hours and the pH of the reaction mixture adjusted to 9-10 with sodium hydroxide. 1-Benzyl-5-hydroxymethyl-imidazole is obtained, 3.8 g (60%), m.p. 131°-135° C.

Sources & evidence

ORD record
ord-f655f798f4df46de975004a0485c55f6
Source dataset
uspto-grants-1986_04
Patent number
US04584383

Linked notes

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