1,1'-Carbonyldiimidazole → N-{2-tert-butyl-3-(4-chlorophenyl)-3-(1-imidazolylcarbonyloxy)propanoyl}-imidazole

HRID 64899Notes

Reaction equation

HRID 64899 reaction equation
[C:1]([CH:5]([CH:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[OH:10])[C:6]([OH:8])=O)([CH3:4])([CH3:3])[CH3:2].[C:18](N1C=CN=C1)([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:19]>O1CCCC1>[C:1]([CH:5]([CH:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[O:10][C:18]([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:19])[C:6]([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 13502818HCID 13502818, compound

Product 1

HCID 13502796N-{2-tert-butyl-3-(4-chlorophenyl)-3-(1-imidazolylcarbonyloxy)propanoyl}-imidazoleYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

83.3 Grams (0.324 mole) of 2-tert-butyl-3-(4-chlorophenyl)-3-hydroxypropionic acid and 125 g (0.77 mole) of 1,1'-carbonyldiimidazole were mixed with 700 ml of tetrahydrofuran, and the mixture was heated under reflux for 3 hours with stirring. After concentrating the reaction solution under reduced pressure, water and then diethyl ether were added to the residue which was then washed with water. The ether layer was separated and concentrated to form crystals with a small amount of ether left in the system. The crystal was filtered off and washed with a small amount of ether to obtain 50.6 g (38.5%) of N-{2-tert-butyl-3-(4-chlorophenyl)-3-(1-imidazolylcarbonyloxy)propanoyl}-imidazole. m.p., 69°-71° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationAfter concentrating the reaction solution under reduced pressure, water
  4. additiondiethyl ether were added to the residue which
  5. washwas then washed with water
  6. customThe ether layer was separated
  7. concentrationconcentrated
  8. customto form crystals with a small amount of ether
  9. waitleft in the system
  10. filtrationThe crystal was filtered off
  11. washwashed with a small amount of ether

Sources & evidence

ORD record
ord-9e5baa0c1d444c6abb03227dbc0ce888
Source dataset
uspto-grants-1986_09
Patent number
US04610997

Reaction notes

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