Aminoacetaldehyde → 1-[alpha-(o-Chlorophenyl)-o-tolyl]imidazole

HRID 267285

Reaction equation

HRID 267285 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH2:11].[CH:16](OC)(OC)OC.[NH2:23][CH2:24][CH:25]=O>C(COC)OC.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[N:11]1[CH:25]=[CH:24][N:23]=[CH:16]1

Participants

6

Reactant 3

HCID 363AminoacetaldehydeHCID 9005Trimethyl orthoformateHCID 134266642-[(2-Chlorophenyl)methyl]aniline

Product 1

HCID 214974091-[alpha-(o-Chlorophenyl)-o-tolyl]imidazole

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

In the manner given in Example 1, α-(0-chlorophenyl)-0-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-(0-chlorophenyl)-0-tolyl]imidazole.

Sources & evidence

ORD record
ord-f06bfcfd0f2d436682cbfdbb504b6f16
Source dataset
uspto-grants-1976_03
Patent number
US03941802

Linked notes

Loading…