Ethanol → HCID 15284527, compound

HRID 260726Notes

Reaction equation

HRID 260726 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]([C:14]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(C(OCC)=O)[C:15]([O:17]CC)=[O:16])=[CH:12][N:11]=[C:10]1[S:32][CH2:33][CH2:34][CH3:35].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O>[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]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:15]([OH:17])=[O:16])=[CH:12][N:11]=[C:10]1[S:32][CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 54294556HCID 54294556, compound

Product 1

HCID 15284527HCID 15284527, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of diethyl [1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]phenylmethyl-malonate (0.66 g, 1.28 mmol), sodium carbonate (1.36 g, 1.28 mmol), ethanol (15 mL) and water (10 mL) was refluxed on a steam bath for 18 hours. The mixture was concentrated to a small volume, some insolubles were filtered, the aqueous layer was washed with diethyl ether and then the aqueous phase was adjusted to pH 3.4 with aqueous hydrochloric acid. The product was extracted into methylene chloride, washed with water, dried and concentrated to give 2-[1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]-3-phenyl-propionic acid; mp 60°-63° C.

Workup

  1. temperaturewas refluxed on a steam bath for 18 hours
  2. concentrationThe mixture was concentrated to a small volume
  3. filtrationsome insolubles were filtered
  4. washthe aqueous layer was washed with diethyl ether
  5. extractionThe product was extracted into methylene chloride
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5cffd24a61984ea485b3a24bfa95c142
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Reaction notes

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