Ethyl orthoformate → 5-Methyl-1-[alpha-(o-chlorophenyl)-o-tolyl]imidazole

HRID 1730469Notes

Reaction equation

HRID 1730469 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](OCC)(OCC)OCC.[CH3:26][C:27]1([CH2:32][NH2:33])OCCO1>[Ti](Cl)(Cl)(Cl)Cl>[CH3:26][C:27]1[N:11]([C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:16]=[N:33][CH:32]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 12434663(2-Methyl-1,3-dioxolan-2-yl)methanamineHCID 134266642-[(2-Chlorophenyl)methyl]aniline

Product 1

HCID 214973875-Methyl-1-[alpha-(o-chlorophenyl)-o-tolyl]imidazole

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

In the manner given in Example 3, α-(o-chlorophenyl)-o-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-(o-chlorophenyl)-o-tolyl]imidazole.

Sources & evidence

ORD record
ord-cc13805fd1e8428d87430670069f7e86
Source dataset
uspto-grants-1976_11
Patent number
US03992400

Reaction notes

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