Trityl chloride → Ethyl 5-methyl-1-(triphenylmethyl)imidazole-4-carboxylate

HRID 847184Notes

Reaction equation

HRID 847184 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:6]([C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 99200Ethyl 4-methyl-5-imidazolcarboxylate

Product 1

HCID 14773935Ethyl 5-methyl-1-(triphenylmethyl)imidazole-4-carboxylateYield 69.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 5-methyl-4-1H-imidazolecarboxylate (6.16 g) in toluene (100 ml), triphenylmethyl chloride (11.12 g) and triethylamine (5.6 ml) were heated at reflux for 18 h. Toluene was removed under reduced pressure and the residue was dissolved in dichloromethane (100 ml), washed with water (4×50 ml) dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica using 1% methanol in dichloromethane as eluant with a trace of triethylamine. This afforded the title compound (11 g), m.p. 188°-190° C. δH (250 MHz, CDCl3) 1.38-1.42 (3 H, t, J=6.5 Hz, CH3), 1.86 (3 H, s, CH3), 4.36-4.40 (2 H, q, J=7.2 Hz, CH2), 7.10-7.46 (16 H, m, ArH); m/z (NoM+), 243 (Ph3C+, 100%).

Workup

  1. temperatureat reflux for 18 h
  2. customToluene was removed under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (100 ml)
  4. washwashed with water (4×50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica using 1% methanol in dichloromethane as eluant with a trace of triethylamine

Sources & evidence

ORD record
ord-22b5e2bcff5a4be48a7495cf4e7174b6
Source dataset
uspto-grants-1992_08
Patent number
US05140034

Reaction notes

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