HCID 13075848, compound → HCID 13228938, compound

HRID 1380549Notes

Reaction equation

HRID 1380549 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18]CC)=[C:14]([CH3:21])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9]>Br>[Cl:1][C:2]1[N:3]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH3:21])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9]

Participants

3

Reactant 1

HCID 13075848HCID 13075848, compound

Product 1

HCID 13228938HCID 13228938, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

4-Chloro-1-(4-ethoxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid (10 g) was stirred in 90 ml of 57% hydrobromic acid at 80°-90° C. for 6 hours. The reaction mixture was evaporated to dryness under reduced pressure and the residue was dissolved in 200 ml of ethyl acetate and washed three times with water. The ethyl acetate layer was evaporated to dryness under reduced pressure and the residue was purified by column chromatography using 210 g of silica gel. The desired fractions were recrystallized from acetone-diethyl ether to give 3 g of 4-chloro-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid as colorless needles, m.p. 190°-192° C. (decompn.).

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in 200 ml of ethyl acetate
  3. washwashed three times with water
  4. customThe ethyl acetate layer was evaporated to dryness under reduced pressure
  5. customthe residue was purified by column chromatography
  6. customThe desired fractions were recrystallized from acetone-diethyl ether

Sources & evidence

ORD record
ord-5832d72d57c041f4bfc2ddb6b2b1677c
Source dataset
uspto-grants-1986_04
Patent number
US04582847

Reaction notes

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