Hydrochloric Acid → HCID 13075865, compound

HRID 223511Notes

Reaction equation

HRID 223511 reaction equation
C([O:8][C:9]1[CH:31]=[CH:30][C:12]([CH2:13][N:14]2[C:18]([CH2:19][C:20]([OH:22])=[O:21])=[C:17]([Cl:23])[N:16]=[C:15]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.Cl>C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:18]([CH2:19][C:20]([OH:22])=[O:21])=[C:17]([Cl:23])[N:16]=[C:15]2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13075843HCID 13075843, compound

Product 1

HCID 13075865HCID 13075865, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.3 g of 1-(4-benzyloxybenzyl)-4-chloro-2-phenylimidazole-5-acetic acid was boiled in 50 ml of ethanol saturated with hydrogen chloride for 7 hours. The reaction solution was evaporated to dryness under reduced pressure, and 50 ml each of a 5% aqueous sodium carbonate solution and ethyl acetate were added to the residue to shake to mix. The ethyl acetate layer was washed and evaporated to dryness under reduced pressure. Recrystallization of the residue from 10 ml of acetonitrile yielded 140 mg of 1-(4-hydroxybenzyl)-4-chloro-2-phenylimidazole-5-acetic acid as colorless crystals, m.p. 196°-199° C.

Workup

  1. customThe reaction solution was evaporated to dryness under reduced pressure, and 50 ml each of a 5% aqueous sodium carbonate solution and ethyl acetate
  2. additionwere added to the residue
  3. additionto mix
  4. washThe ethyl acetate layer was washed
  5. customevaporated to dryness under reduced pressure
  6. customRecrystallization of the residue from 10 ml of acetonitrile

Sources & evidence

ORD record
ord-96a31a869fe346d0bf010898bed0a193
Source dataset
uspto-grants-1982_10
Patent number
US04355040

Reaction notes

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