Methanol → HCID 66657784, compound

HRID 420570Notes

Reaction equation

HRID 420570 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([O:12][CH2:13][CH2:14][N:15]2[CH:20]([CH3:21])[CH2:19][N:18]([C:22]3[S:23][C:24]([Br:27])=[CH:25][N:26]=3)[CH2:17][CH:16]2[CH3:28])[CH:6]=1.[OH-].[Na+].CO.O1CCCC1>[Cl-].[Na+].O.O>[Br:27][C:24]1[S:23][C:22]([N:18]2[CH2:19][CH:20]([CH3:21])[N:15]([CH2:14][CH2:13][O:12][C:7]3[CH:6]=[C:5]([CH2:4][C:3]([OH:29])=[O:2])[CH:10]=[CH:9][C:8]=3[CH3:11])[CH:16]([CH3:28])[CH2:17]2)=[N:26][CH:25]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66657722HCID 66657722, compound

Product 1

HCID 66657784HCID 66657784, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of [3-[2-[4-(5-bromothiazole-2-yl)-2,6-dimethyl piperazine-1-yl]ethoxy]-4-methylphenyl]acetic acid methyl ester (8.49 g), 2N aqueous sodium hydroxide solution (22 mL), methanol (50 mL) and tetrahydrofuran (50 mL) was stirred at room temperature for 1.5 hours. To the reaction solution were added water and brine. The mixture was washed with ethyl acetate. The water layer was neutralized with 2N hydrochloric acid and extracted with chloroform. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was washed with diisopropyl ether to give the title compound (5.81 g).

Workup

  1. washThe mixture was washed with ethyl acetate
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-697caa07e91f498c8f20e40fa6e99cfd
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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