Trityl chloride → Ethyl 1-trityl-1H-imidazole-4-carboxylate

HRID 2107775Notes

Reaction equation

HRID 2107775 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:3]=[CH:2]1.C(N(CC)CC)C.[C:18](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[C:18]([N:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:3]=[CH:2]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178469898HCID 178469898, compound

Product 1

HCID 618225Ethyl 1-trityl-1H-imidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of ethyl imidazole-4-carboxylate (1.4 g), triethylamine (1.2 g) and chloroform (20 ml) was stirred at room temperature while trityl chloride (3.06 g) was added, and the mixture was stirred at room temperature for 1 h. The resulting solution was washed with water, dried and evaporated to dryness under reduced pressure, and the residue was crystallised from a mixture of ethyl acetate and cyclohexane, to give ethyl 1-tritylimidazole-4-carboxylate, mp 163°-164°.

Workup

  1. additionwas added
  2. washThe resulting solution was washed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. customthe residue was crystallised from a mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-07f27815e0ab4364a316f9a5418edb32
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

Loading…