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

HRID 1730467Notes

Reaction equation

HRID 1730467 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 Example 1, 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-81a992cc110d4c3ca100eaea71f2ca7d
Source dataset
uspto-grants-1976_11
Patent number
US03992400

Reaction notes

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