Water → HCID 13228938, compound

HRID 1380547Notes

Reaction equation

HRID 1380547 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([CH3:20])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9].O>Br.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH3:20])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 962WaterHCID 12822158HCID 12822158, compound

Product 1

HCID 13228938HCID 13228938, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-1-(4-methoxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid (2.2 g) was stirred in 20 ml of 57% hydrobromic acid at 100°-110° C. for 2 hours. To the reaction mixture was then added 80 ml of water and the mixture was allowed to stand. The resulting syrupy precipitate was dissolved in 50 ml of ethyl acetate and washed with water. The ethyl acetate layer was evaporated to dryness and the residue was purified by column chromatography using 50 g of silica gel. The desired fractions were combined and crystallized from acetone-diethyl ether to give 0.3 g of 4-chloro-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid as colorless needles, m.p. 190°-193° C. (decompn.).

Workup

  1. washwashed with water
  2. customThe ethyl acetate layer was evaporated to dryness
  3. customthe residue was purified by column chromatography
  4. customcrystallized from acetone-diethyl ether

Sources & evidence

ORD record
ord-460a509784634a16a1ba6928dbe74d0c
Source dataset
uspto-grants-1986_04
Patent number
US04582847

Reaction notes

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