Hydrochloric Acid → HCID 22400421, compound

HRID 2254287Notes

Reaction equation

HRID 2254287 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][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])=[CH:12][N:11]=[C:10]1[S:22][CH2:23][CH2:24][CH3:25].[OH-].[K+].Cl>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]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:12][N:11]=[C:10]1[S:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19743676ethyl 4-[1 (2-chlorophenyl)methyl-2-propylthio-1H-imidazol-5-yl]butyrate

Product 1

HCID 22400421HCID 22400421, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of ethyl 4-[1 (2-chlorophenyl)methyl-2-propylthio-1H-imidazol-5-yl]butyrate (244 mg) was dissolved in ethanol (5 mL) and a solution of potassium hydroxide (950 mg) in water (5 mL) was added. After being stirred at room temperature for 2 hours, the solution was diluted with water, acidified to pH 3.5 to 4.0 with 10% hydrochloric acid solution and the precipitated product was filtered, washed well with water and recrystallized from acetonitrile to afford 0.144 g (64%) of 4-[1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazol-5-yl]butyric acid; mp 98°-99° C.

Workup

  1. filtrationthe precipitated product was filtered
  2. washwashed well with water
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-6bbdd5b4712e43d3a8d1a9c7754c900e
Source dataset
uspto-grants-1993_08
Patent number
US05234917

Reaction notes

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