Water → HCID 15284531, compound

HRID 260741Notes

Reaction equation

HRID 260741 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:13]([CH2:14][C:15]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(C(OCC)=O)[C:16]([O:18]CC)=[O:17])=[CH:12][N:11]=[C:10]1[S:33][CH2:34][CH2:35][CH3:36].[OH-].[K+].O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:13]([CH2:14][CH:15]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:16]([OH:18])=[O:17])=[CH:12][N:11]=[C:10]1[S:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 86748911HCID 86748911, compound

Product 1

HCID 15284531HCID 15284531, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl [1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]methyl-2-benzyl-malonate (0.72 g, 1.36 mmol), potassium hydroxide (0.83 g, 14.7 mmol), water (15 mL) and ethanol (25 mL) was refluxed for 4 hours. The ethanol was evaporated, the residual aqueous layer was extracted with diethyl ether, and the basic solution was adjusted to pH 3.75 with concentrated hydrochloric acid. The precipitated product was extracted into methylene chloride, dried, and concentrated. This crude product was flash chromatographed on silica gel with 10% methanol in methylene chloride to give 0.51 g (86%) of 3-[1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]-2-benzylpropanoic acid; mp 123°-127° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe ethanol was evaporated
  3. extractionthe residual aqueous layer was extracted with diethyl ether
  4. extractionThe precipitated product was extracted into methylene chloride
  5. customdried
  6. concentrationconcentrated
  7. customchromatographed on silica gel with 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-39f17be38602424480663b9df7ee2851
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Reaction notes

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