HCID 13768101, compound → N-diethylphosphoryl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide

HRID 1789355Notes

Reaction equation

HRID 1789355 reaction equation
[CH2:1]([P:3]([N:7]=[C:8]=[S:9])([CH2:5][CH3:6])=[O:4])[CH3:2].[F:10][C:11]1[CH:12]=[C:13]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH:32]3[NH:36][CH2:35][CH2:34][S:33]3)[CH2:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1>CC(C)=O>[CH2:1]([P:3]([NH:7][C:8]([N:36]1[CH2:35][CH2:34][S:33][CH:32]1[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[O:25][CH2:24][CH2:23][N:20]1[CH2:19][CH2:18][N:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([F:10])[CH:12]=2)[CH2:22][CH2:21]1)=[S:9])([CH2:5][CH3:6])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 13768101HCID 13768101, compoundHCID 20188170Diethylphosphoryl isothiocyanate

Product 1

HCID 14095401N-diethylphosphoryl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.68 g of diethylphosphoryl isothiocyanate is added to a solution of 1.23 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine in 20 ml of acetone, and the mixture is stirred for one day. The mixture is concentrated under reduced pressure to remove solvent. The residue is extracted with chloroform, and the extract is washed with a saturated sodium chloride solution, dried and concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, chloroform:methanol=40:1), and the resultant product is recrystallized from ethyl acetate and ether. 1.49 g of N-diethylphosphoryl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide are obtained. Yield: 81%.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customto remove solvent
  3. extractionThe residue is extracted with chloroform
  4. washthe extract is washed with a saturated sodium chloride solution
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto remove solvent
  8. customThe residue is purified by silica gel chromatography (solvent, chloroform:methanol=40:1)
  9. customthe resultant product is recrystallized from ethyl acetate and ether

Sources & evidence

ORD record
ord-1bfbce77124b4ef7b75e6c9cc7cb718a
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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