Sodium Hydroxide → 2-(4-Fluorophenyl)4-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoic acid

HRID 1251936Notes

Reaction equation

HRID 1251936 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([O:24][CH2:25][CH2:26][C:27]1[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=1)[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[C:9]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:8]=1.[OH-].[Na+]>CO.O>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:9]2[CH:8]=[C:7]([CH:6]([O:24][CH2:25][CH2:26][C:27]3[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=3)[C:2]3[S:1][CH:5]=[CH:4][N:3]=3)[CH:16]=[CH:15][C:10]=2[C:11]([OH:13])=[O:12])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18324500Methyl 4-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]-2-(4-fluorophenyl)benzoate

Product 1

HCID 183244862-(4-Fluorophenyl)4-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 4-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]-2-(4-fluorophenyl)benzoate (1.45 g, 3.21 mmol) and sodium hydroxide (0.64 g, 16.05 mmol) in methanol (75 ml) and water (7 ml) was stirred under a nitrogen atmosphere at reflux for 18 hours, cooled to ambient temperature and the methanol evaporated off. The residue was treated with aqueous citric acid (1M, 5 ml) and extracted with dichloromethane. The organic extracts were dried and evaporated to dryness to give 2-(4-fluorophenyl)-4-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoic acid as a white foam, (0.877 g, 63%).

Workup

  1. temperatureat reflux for 18 hours
  2. customthe methanol evaporated off
  3. additionThe residue was treated with aqueous citric acid (1M, 5 ml)
  4. extractionextracted with dichloromethane
  5. customThe organic extracts were dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f0cc959e2828485f9df8497d45187870
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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