Hydrochloric Acid → HCID 178479683, compound

HRID 2072048Notes

Reaction equation

HRID 2072048 reaction equation
[CH2:1]([C:8]1[N:9]=[CH:10][NH:11][C:12]=1[C:13](OCC)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[ClH:25]>O1CCCC1>[ClH:25].[CH2:1]([C:8]1[N:9]=[CH:10][NH:11][C:12]=1[CH2:13][OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178470401HCID 178470401, compound

Product 1

HCID 178479683HCID 178479683, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of this aminoketone (160 g.) with formamide (480 ml.) by heating at 120°-140° over five hours gave 4-benzyl-5-carbethoxyimidazole (75 g.) m.p. 168.5°-169.5°. Reduction of this ester (30 g.) with lithium aluminum hydride (6.4 g.) in tetrahydrofuran (600 ml.), followed by addition of water, filtration and acidification of the filtrate with ethanolic hydrogen chloride, gave 4-benzyl-5-hydroxymethylimidazole hydrochloride (22.9 g.), m.p. 149°-151°, after concentration and addition of ethyl acetate.

Sources & evidence

ORD record
ord-e7ad6cf3bca7466982b37598cf5adbe6
Source dataset
uspto-grants-1977_09
Patent number
US04049672

Reaction notes

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