Hydrochloric Acid → 2-((E)-2-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}ethenyl)-1,3-thiazole-4-carboxylic acid

HRID 2221881Notes

Reaction equation

HRID 2221881 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:46])=[C:9]([CH2:11][O:12][C:13]2[CH:43]=[CH:42][C:16]([CH2:17][O:18][C:19]3[C:23](/[CH:24]=[CH:25]/[C:26]4[S:27][CH:28]=[C:29]([C:31]([O:33]CC)=[O:32])[N:30]=4)=[CH:22][N:21]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[N:20]=3)=[CH:15][C:14]=2[O:44][CH3:45])[N:10]=1.O1CCCC1.[OH-].[Na+].Cl>O.C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:46])=[C:9]([CH2:11][O:12][C:13]2[CH:43]=[CH:42][C:16]([CH2:17][O:18][C:19]3[C:23](/[CH:24]=[CH:25]/[C:26]4[S:27][CH:28]=[C:29]([C:31]([OH:33])=[O:32])[N:30]=4)=[CH:22][N:21]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[N:20]=3)=[CH:15][C:14]=2[O:44][CH3:45])[N:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69216223ethyl 2-((E)-2-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}ethenyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 692140952-((E)-2-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}ethenyl)-1,3-thiazole-4-carboxylic acidYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of ethyl 2-((E)-2-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}ethenyl)-1,3-thiazole-4-carboxylate (0.13 g), tetrahydrofuran (1 mL) and ethanol (1 mL) was added 1N aqueous sodium hydroxide solution (1 mL), and the mixture was heated under reflux for 1 hr. To the reaction mixture were added 1N hydrochloric acid (1 mL) and water, and the precipitated crystals were collected by filtration to give 2-((E)-2-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}ethenyl)-1,3-thiazole-4-carboxylic acid as yellow crystals (0.08 g, yield 67%). Recrystallization from tetrahydrofuran-hexane gave yellow prism crystals. melting point: 170-172° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-44eef6a88f1247298b3b67bb6edab9ec
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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