Hydrochloric Acid → 2-carbethoxy-3-[1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]propanoic acid

HRID 260729Notes

Reaction equation

HRID 260729 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][CH:15]([C:21]([O:23]CC)=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][N:11]=[C:10]1[S:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[Na+].[Na+].C(O)C.Cl>O>[C:16]([CH:15]([CH2:14][C:13]1[N:9]([CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:10]([S:26][CH2:27][CH2:28][CH3:29])=[N:11][CH:12]=1)[C:21]([OH:23])=[O:22])([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 86748910diethyl [1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]methylmalonate

Product 1

HCID 152845282-carbethoxy-3-[1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]propanoic acidYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of diethyl [1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]methylmalonate (0.62 g, 1.41 mmol), sodium carbonate (1.5 g, 14.2 mol), ethanol (10 mL) and water (10 mL) was stirred at 25° C. for 18 hours, then heated for 15 minutes on a steam bath. The mixture was cooled, neutralized with aqueous hydrochloric acid solution, and the product was extracted into methylene chloride, washed with water, dried and concentrated to 0.425 g of product. Crystallization from ethyl acetate/hexane provided 0.23 g (55%) of 2-carbethoxy-3-[1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]propanoic acid; mp 118°-120° C.

Workup

  1. temperatureheated for 15 minutes on a steam bath
  2. temperatureThe mixture was cooled
  3. extractionthe product was extracted into methylene chloride
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated to 0.425 g of product
  7. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-93bceb6137e7427789774bb17aa102b6
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Reaction notes

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