HCID 54019290, compound → HCID 70410509, compound

HRID 638620Notes

Reaction equation

HRID 638620 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH:5]=[CH:6][C:7]=1[C:8]([O:10]CC)=[O:9]>Cl>[OH2:9].[ClH:1].[C:8]([C:7]1[CH:6]=[CH:5][C:4]([CH:13]=[CH:14][CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)=[CH:3][C:2]=1[Cl:1])([OH:10])=[O:9].[C:8]([C:7]1[CH:6]=[CH:5][C:4]([CH:13]=[CH:14][CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)=[CH:3][C:2]=1[Cl:1])([OH:10])=[O:9].[ClH:1]

Participants

3

Reactant 1

HCID 54019290HCID 54019290, compound

Product 1

HCID 70410509HCID 70410509, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1-[3-(3-chloro-4-ethoxycarbonylphenyl)prop-2-enyl]imidazole (0.09 g) in hydrochloric acid (3 ml, 6M) was stirred and heated under reflux for 3 h. The reaction mixture was concentrated under reduced pressure, and toluene (10 ml) was added and the reaction mixture re-concentrated. Repetition of the toluene/concentration procedure three times afforded a white solid which was recrystallised from ethyl acetate/ethanol/ether to give 1-[3-(4-carboxy-3-chlorophenyl)prop-2-enyl]imidazole hydrochloride hemihydrate as a white crystalline solid, m.p. 247°-249°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and toluene (10 ml)
  4. additionwas added
  5. concentrationthe reaction mixture re-concentrated
  6. concentrationRepetition of the toluene/concentration procedure three times
  7. customafforded a white solid which
  8. customwas recrystallised from ethyl acetate/ethanol/ether

Sources & evidence

ORD record
ord-2fcf44cb50ee4e1c886f59a4b79913af
Source dataset
uspto-grants-1985_12
Patent number
US04562199

Reaction notes

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