Sodium Hydroxide → HCID 13768048, compound

HRID 1789361Notes

Reaction equation

HRID 1789361 reaction equation
C([NH:4][C:5]([N:7]1[CH2:11][CH2:10][S:9][CH:8]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH2:23][CH2:22]1)=[S:6])(=O)C.[OH-].[Na+]>C(O)C>[F:33][C:29]1[CH:28]=[C:27]([N:24]2[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][O:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH:8]3[N:7]([C:5](=[S:6])[NH2:4])[CH2:11][CH2:10][S:9]3)[CH2:22][CH2:23]2)[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13768030HCID 13768030, compound

Product 1

HCID 13768048HCID 13768048, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.87 g of N-acetyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide, 7.3 ml of 10% aqueous sodium hydroxide solution and 60 ml of ethanol is refluxed for 20 hours and then concentrated under reduced pressure to remove solvent. The residue is extracted with ethyl acetate, and the extract is washed with a saturated sodium chloride solution, dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, chloroform:ethyl acetate=2:1). 2.36 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide are obtained. Yield: 90%.

Workup

  1. temperatureis refluxed for 20 hours
  2. concentrationconcentrated under reduced pressure
  3. customto remove solvent
  4. extractionThe residue is extracted with ethyl acetate
  5. washthe extract is washed with a saturated sodium chloride solution
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto remove solvent
  9. customThe residue is purified by silica gel chromatography (solvent, chloroform:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-f2ba0d33acd149c78f546b6cef92101a
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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