Ethyl orthoformate → 5-Methyl-1-(alpha-phenyl-o-tolyl)imidazole

HRID 267283

Reaction equation

HRID 267283 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](OCC)(OCC)OCC.[CH3:25][C:26]1([CH2:31][NH2:32])OCCO1>[Ti](Cl)(Cl)(Cl)Cl>[CH3:25][C:26]1[N:10]([C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:15]=[N:32][CH:31]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 1198052-BenzylanilineHCID 12434663(2-Methyl-1,3-dioxolan-2-yl)methanamine

Product 1

HCID 214973675-Methyl-1-(alpha-phenyl-o-tolyl)imidazole

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

In the manner given in Example 3, α-phenyl-0-toluidine is reacted with triethyl orthoformate, the resulting oil is heated with 2-methyl-2-(aminomethyl)-1,3-dioxolane, and the resulting product treated with titanium tetrachloride to give 5-methyl-1-(α-phenyl-0-tolyl)imidazole.

Sources & evidence

ORD record
ord-3db1208e59ab41ed99adb07321ca5a78
Source dataset
uspto-grants-1976_03
Patent number
US03941802

Linked notes

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