Hydrochloric Acid → 3-[4-(3,4-Dimethylphenyl)-2-thiazolyl]benzoic acid

HRID 1264958Notes

Reaction equation

HRID 1264958 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=3)[C:17]([O:19]CC)=[O:18])[S:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=3)[C:17]([OH:19])=[O:18])[S:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18613842Ethyl 3-[4-(3,4-dimethylphenyl)-2-thiazolyl]benzoate

Product 1

HCID 186138193-[4-(3,4-Dimethylphenyl)-2-thiazolyl]benzoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-[4-(3,4-dimethylphenyl)-2-thiazolyl]benzoate (1.25 g), a 1N aqueous solution of sodium hydroxide (10 ml), tetrahydrofuran (10 ml) and ethanol (10 ml) was stirred at 60 to 70° C. for 1 hour. The reaction mixture was poured into 1N hydrochloric acid, and precipitated crystals were collected by filtration, and then washed with water. The product was recrystallized from acetone-hexane to obtain 3-[4-(3,4-dimethylphenyl)-2-thiazolyl]benzoic acid (825 mg, yield: 72%). Colorless prisms. Melting point: 235 to 236° C.

Workup

  1. customprecipitated crystals
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customThe product was recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-ed3063c2e2cb4973b8b8e6df49903768
Source dataset
uspto-grants-2003_04
Patent number
US06545009B1

Reaction notes

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