Sodium Hydroxide → HCID 10002389, compound

HRID 1033893Notes

Reaction equation

HRID 1033893 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:32])[C:7](/[C:10](/[CH3:24])=[C:11](\[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[C:12]([O:14]CC)=[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]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:32])[C:7](/[C:10](/[CH3:24])=[C:11](\[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[C:12]([OH:14])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 10003933HCID 10003933, compound

Product 1

HCID 10002389HCID 10002389, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-benzyl-2-butenoate (623 mg, 1.38 mmol) in ethanol (25 mL) under argon was treated with 10% sodium hydroxide solution (20 mL), and then stirred for 1 hour at room temperature. An additional 25 mL of 10% sodium hydroxide were added and the mixture was stirred overnight at ambient temperature. Acidification to pH 4 with dilute hydrochloric acid solution followed by extraction with methylene chloride and washing with water gave after drying and workup, 630 mg of crude product. Trituration with ethyl acetate/ether provided the title compound (302 mg, 52%), mp 206°-207° C., as the white hydrochloride salt.

Workup

  1. stirringthe mixture was stirred overnight at ambient temperature
  2. extractionAcidification to pH 4 with dilute hydrochloric acid solution followed by extraction with methylene chloride
  3. washwashing with water
  4. customgave
  5. customafter drying

Sources & evidence

ORD record
ord-3fabfd148fd549a0843d03dcd4099050
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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