Aminoacetaldehyde → 1-(alpha-Phenyl-o-tolyl)imidazole

HRID 267416

Reaction equation

HRID 267416 reaction equation
[C:1]1([CH2:7][C:8]2[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15](OC)(OC)OC.[NH2:22][CH2:23][CH:24]=O>C(COC)OC.[Ti](Cl)(Cl)(Cl)Cl>[C:1]1([CH2:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]2[CH:24]=[CH:23][N:22]=[CH:15]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 363AminoacetaldehydeHCID 9005Trimethyl orthoformateHCID 1198052-Benzylaniline

Product 1

HCID 214973581-(alpha-Phenyl-o-tolyl)imidazole

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

In the manner given in Preparation 21, α-phenyl-o-toluidine is reacted first with trimethyl orthoformate, the resulting product is reacted with aminoacetaldehyde, dimethyl acetal, and the resulting product of this reaction is heated with titanium tetrachloride in monoglyme to give 1-(α-phenyl-o-tolyl)imidazole.

Sources & evidence

ORD record
ord-95c6e07595134a3592a956073228a28d
Source dataset
uspto-grants-1976_03
Patent number
US03941803

Linked notes

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