Potassium Carbonate → HCID 9884304, compound

HRID 1757169Notes

Reaction equation

HRID 1757169 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]([CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])=[CH:12][N:11]=[C:10]1[S:21][CH2:22][CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>O.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:13]([CH:14]([CH3:20])[C:15]([OH:17])=[O:16])=[CH:12][N:11]=[C:10]1[S:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 22400434HCID 22400434, compound

Product 1

HCID 9884304HCID 9884304, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 2-[1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]propionate (0.71 g, 1.94 mmol) in water (10 mL) and methanol (5 mL) was treated with potassium carbonate (0.51 g, 3.7 mmol). The reaction mixture was refluxed on a steam bath for 2 hours, the methanol was evaporated, the aqueous layer was washed with diethyl ether, cooled in ice, and adjusted to pH 3.4 with aqueous hydrochloric acid solution. The resulting gummy solid was extracted into methylene chloride, washed with water, dried, and concentrated. The residue was triturated with diethyl ether to give 2-[1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]propionic acid; mp 170°-172° C.

Workup

  1. temperatureThe reaction mixture was refluxed on a steam bath for 2 hours
  2. customthe methanol was evaporated
  3. washthe aqueous layer was washed with diethyl ether
  4. temperaturecooled in ice
  5. extractionThe resulting gummy solid was extracted into methylene chloride
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-3f453cea468c495483333e0d94335a78
Source dataset
uspto-grants-1995_08
Patent number
US05444080

Reaction notes

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