Sodium Hydroxide → HCID 9844411, compound

HRID 2081853Notes

Reaction equation

HRID 2081853 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:7](/[CH:10]=[C:11](\[CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)/[C:12]([O:14]C)=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C(O)C>[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:7](/[CH:10]=[C:11](\[CH2:16][C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)/[C:12]([OH:14])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10387616HCID 10387616, compound

Product 1

HCID 9844411HCID 9844411, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of methyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(4-pyridyl)methyl-2-propenoate (3.1 g, 7.3 mmol) in ethanol (16 mL) was treated with 10% sodium hydroxide solution and the mixture was stirred for 18 hours at 25° C. The solution was concentrated in vacuum, water was added, the pH was adjusted to 6.5 and the resulting solid was filtered, washed with water and crystallized from methanol/ether to afford 0.48 g of (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(4-pyridyl)methyl-2-propenoic acid; mp 178°-182° C. (d).

Workup

  1. concentrationThe solution was concentrated in vacuum, water
  2. additionwas added
  3. filtrationthe resulting solid was filtered
  4. washwashed with water
  5. customcrystallized from methanol/ether

Sources & evidence

ORD record
ord-32676e925d0346179727d6c001b866c5
Source dataset
uspto-grants-1993_02
Patent number
US05185351

Reaction notes

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