Hydroquinone → 1-(1-ethoxyethyl)-2-methyl-4,5-diphenyl-1H-imidazole

HRID 1085815Notes

Reaction equation

HRID 1085815 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH:19]([O:21][CH2:22][CH3:23])=[CH2:20].C1(C=CC(O)=CC=1)O>>[CH2:19]([O:21][CH:22]([N:6]1[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=[C:2]1[CH3:1])[CH3:23])[CH3:20]

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 8023Ethyl vinyl etherHCID 2366964,5-Diphenyl-2-methylimidazole

Product 1

HCID 103804501-(1-ethoxyethyl)-2-methyl-4,5-diphenyl-1H-imidazoleYield 68.3%

Conditions

Temperature
180 °C

Procedure

A mixture of 2-methyl-4,5-diphenylimidazole (3.00 g, l3 mmol), ethyl vinyl ether (9.23 g, l2.30 mL, l30 mmol) and hydroquinone (0.l4 g, l.2 mmol) was heated at 180° C. in a sealed vessel for 17 hours. The excess ethyl vinyl ether was evaporated and the residue chromatographed on a column of silica gel using a mixture of diethyl ether and hexanes (3:2) as eluent. Elution gave 1-(1-ethoxyethyl)-2-methyl-4,5-diphenyl-1H-imidazole (2.68 g, 68%), mp 87°-89° C.

Workup

  1. customThe excess ethyl vinyl ether was evaporated
  2. customthe residue chromatographed on a column of silica gel using
  3. additiona mixture of diethyl ether and hexanes (3:2) as eluent
  4. washElution

Sources & evidence

ORD record
ord-af8c30be77994bf8ad2a5b5fbb4997e9
Source dataset
uspto-grants-1991_04
Patent number
US05011851

Reaction notes

Loading…