Imidazole → Tert-butyloxycarbonylimidazole

HRID 4427

Reaction equation

HRID 4427 reaction equation
[C:1](=[O:14])(OC(Cl)C(Cl)(Cl)Cl)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[C:3]([O:2][C:1]([C:16]1[NH:15][CH:19]=[CH:18][N:17]=1)=[O:14])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 2724535Tert-butyl 1,2,2,2-tetrachloroethyl Carbonate

Product 1

HCID 22359409Tert-butyloxycarbonylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

5 g (17.5 mmol) of tert-butyl 1,2,2,2-tetrachloroethyl carbonate dissolved in 10 ml of THF are added at 0° C. to a solution of imidazole (1.2 g; 17.6 mmol) in THF (20 ml) in the presence of 5M aqueous potassium carbonate solution (5 ml). The mixture is stirred for 1 hour at 20° C., and the organic phase is decanted and washed with 10 ml of saturated aqueous NaCl solution.

Workup

  1. customthe organic phase is decanted
  2. washwashed with 10 ml of saturated aqueous NaCl solution

Sources & evidence

ORD record
ord-18ed9719ba5540d59af2fe55eab3dddb
Source dataset
uspto-grants-1988_02
Patent number
US04725680

Linked notes

Loading…