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Hydrochloric Acid → 1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carboxylic acid

HRID 350328
Notes
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Reaction equation

HRID 350328 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:35]=[CH:34][C:17]([CH2:18][N:19]4[CH:23]=[C:22]([C:24]([O:26]CC)=[O:25])[C:21]([C:29]5[S:30][CH:31]=[CH:32][CH:33]=5)=[N:20]4)=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:35]=[CH:34][C:17]([CH2:18][N:19]4[CH:23]=[C:22]([C:24]([OH:26])=[O:25])[C:21]([C:29]5[S:30][CH:31]=[CH:32][CH:33]=5)=[N:20]4)=[CH:16][CH:15]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23024852ethyl 1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 230248021-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carboxylic acidYield 90.4%

Reagents, catalysts & solvents

1
HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carboxylate (750 mg), 1N aqueous sodium hydroxide solution (3 ml), tetrahydrofuran (5 ml), and ethanol (5 ml) was stirred at 80° C. for 5 hours. After cooling, 1N hydrochloric acid (3 ml) was added to the mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The resulting colorless crystals were collected by filtration to obtain 1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carboxylic acid (640 mg, yield: 90%). This was recrystallized from acetone-hexane. Melting point: 187˜188° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. filtrationThe resulting colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-39cb42de04604824bb701b0e808fda20
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179823B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes