Sodium Hydroxide → HCID 18471036, compound

HRID 2228712Notes

Reaction equation

HRID 2228712 reaction equation
[C:1]1([CH:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:8][S:9]([C:11]2[S:12][C:13]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[O:24][CH2:25][C:26]([O:28]CC)=[O:27])[C:14]=3[N:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1.CO>[C:31]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][S:9]([C:11]2[S:12][C:13]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[O:24][CH2:25][C:26]([OH:28])=[O:27])[C:14]=3[N:15]=2)=[O:10])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54254648HCID 54254648, compound

Product 1

HCID 18471036HCID 18471036, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [(2-(2,2-diphenylethylsulfinyl)-4,5-dihydronaphtho[1,2-d]thiazol-6-yl)oxy]acetate (0.50 g, 0.965 mmol) in a mixture of tetrahydrofuran (16 mL) and methanol (4 mL) was added 1N-aqueous sodium hydroxide (2 mL) dropwise, and the mixture was stirred at room temperature for 20 minutes. After the solvent was distilled off under reduced pressure, 1N-hydrochloric acid was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried over MgSO4, filtered, and concentrated under reduced pressure to provide 0.36 g of the title compound as amorphous solid. Yield 76%.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure, 1N-hydrochloric acid
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b2fd604834848c4ae47f1831df02b73
Source dataset
uspto-grants-2002_07
Patent number
US06417213B2

Reaction notes

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