Sodium Hydroxide → 3-[2-(Thiazol-2-yl)-3-(imidazol-1-yl)prop-1-en-1-yl]-5-phenylbenzoic acid

HRID 2228023Notes

Reaction equation

HRID 2228023 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([CH2:24][N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1)=[CH:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=1)[C:11]([O:13]C)=[O:12].[OH-].[Na+]>CO>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([CH2:24][N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1)=[CH:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=1)[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54338365Methyl 3-[2-(thiazol-2-yl)-3-(imidazol-1-yl)prop-1-en-1-yl]-5-phenylbenzoate

Product 1

HCID 537066863-[2-(Thiazol-2-yl)-3-(imidazol-1-yl)prop-1-en-1-yl]-5-phenylbenzoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-[2-(thiazol-2-yl)-3-(imidazol-1-yl)prop-1-en-1-yl]-5-phenylbenzoate (Z isomer) (1.41 g; 3.5 mmol) in methanol (15 ml) was heated at reflux with 2N aqueous sodium hydroxide solution (4.4 ml; 8.79 mmol) for 5 hours. Methanol was then evaporated and the solution acidified to pH 6 with 6N HCl. The resulting precipitate was triturated with ethanol/ether to give 3-[2-(thiazol-2-yl)-3-(imidazol-1-yl)prop-1-en-1-yl]-5-phenylbenzoic acid as a solid.

Workup

  1. customMethanol was then evaporated
  2. customThe resulting precipitate was triturated with ethanol/ether

Sources & evidence

ORD record
ord-5c2b430219a64baaac585708dc9856b5
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

Loading…