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

HRID 260733Notes

Reaction equation

HRID 260733 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:7]([CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>C(O)C.O>[CH2:1]([C:5]1[N:6]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:7]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53712560ethyl 3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-propanoate

Product 1

HCID 103361653-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]propanoic acidYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of ethyl 3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]propanoate (179 mg, 0.513 mmol) in ethanol (10 mL) was treated with sodium hydroxide (62 mg, 1.54 mmol) dissolved in water (2 mL). The solution was stirred for one hour at 25° C., cooled, acidified with 10% aqueous hydrochloric acid solution to pH 4.2 and concentrated to near dryness in vacuo. Water (3 mL) was added, and the resulting white solid was filtered, washed with water and dried to give 32 mg (20%) of 3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]propanoic acid; mp 163.5°-164.5° C.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. additionWater (3 mL) was added
  4. filtrationthe resulting white solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-99819e53264844de830c552b6108d050
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Reaction notes

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