Hydrochloric Acid → 2-[2-[4-[(2-Phenyl-4-thiazolyl)methoxy]benzyloxy]phenyl]acetic acid

HRID 1294280Notes

Reaction equation

HRID 1294280 reaction equation
Cl[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:12][CH:13]=2)=[CH:5][CH:4]=1.[OH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][C:30]([O:32]C)=[O:31].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[C:14]1([C:11]2[S:12][CH:13]=[C:9]([CH2:8][O:7][C:6]3[CH:20]=[CH:21][C:3]([CH2:2][O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:29][C:30]([OH:32])=[O:31])=[CH:4][CH:5]=3)[N:10]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 89719Methyl (2-hydroxyphenyl)acetateHCID 178613834-(4-Chloromethylphenoxy)methyl-2-phenylthiazole

Product 1

HCID 688845582-[2-[4-[(2-Phenyl-4-thiazolyl)methoxy]benzyloxy]phenyl]acetic acidYield 29.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(4-chloromethylphenoxymethyl)-2-phenylthiazole (1.95 g), methyl 2-(2-hydroxyphenyl)acetate (1.00 g), anhydrous potassium carbonate (0.85 g) and N,N-dimethylformamide (15 mL) was stirred overnight at room temperature. The reaction mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. To a mixture of the obtained residue, tetrahydrofuran (10 mL) and methanol (10 mL) was added a 1N aqueous sodium hydroxide solution (10 mL) and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated, and dilute hydrochloric acid was added to the residue. The precipitated solid was collected by filtration and dried with air to give crystals (0.76 g, 29%) of 2-[2-[4-[(2-phenyl-4-thiazolyl)methoxy]benzyloxy]phenyl]acetic acid. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 115-116° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. additionTo a mixture of the obtained residue, tetrahydrofuran (10 mL) and methanol (10 mL)
  6. additionwas added a 1N aqueous sodium hydroxide solution (10 mL)
  7. stirringthe mixture was stirred at room temperature for 2 hrs
  8. concentrationThe reaction mixture was concentrated
  9. additiondilute hydrochloric acid was added to the residue
  10. filtrationThe precipitated solid was collected by filtration
  11. customdried with air

Sources & evidence

ORD record
ord-b9e5aa6b35f34ee5b149d48515a5773c
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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