Water → HCID 15284531, compound

HRID 1757184Notes

Reaction equation

HRID 1757184 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 gl 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-{(2chlorophenyl)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-7e8a069b6d3f4714b59cbd5ea4f2e6b1
Source dataset
uspto-grants-1995_08
Patent number
US05444080

Reaction notes

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