Cilostamide → 6-[3-(N-cyclohexyl-N-methylaminothiocarbonyl)propoxy]carbostyril

HRID 2257908Notes

Reaction equation

HRID 2257908 reaction equation
[CH:1]1([N:7]([CH3:25])[C:8]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH:18]=[CH:17]3)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27]>C1C=CC=CC=1>[CH:1]1([N:7]([CH3:25])[C:8]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH:18]=[CH:17]3)=[S:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2753CilostamideHCID 14817Phosphorus sulfide (P2S5)

Product 1

HCID 543234996-[3-(N-cyclohexyl-N-methylaminothiocarbonyl)propoxy]carbostyrilYield 200.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 13.7 g of 6-[3-(N-cyclohexyl-N-methylaminocarbonyl)propoxy]carbostyril and 4.45 g of phosphorus pentasulfide in 200 ml of benzene was refluxed for 5 hours. The reaction mixture was allowed to cool. The insolubles were removed by filtration. The filtrate was subjected to distillation to remove the solvent. The resulting residue was purified by a silica gel column chromatography (eluant: 5% methanol/dichloromethane) to obtain 7.2 g of 6-[3-(N-cyclohexyl-N-methylaminothio-carbonyl)propoxy]carbostyril.

Workup

  1. temperatureto cool
  2. customThe insolubles were removed by filtration
  3. distillationThe filtrate was subjected to distillation
  4. customto remove the solvent
  5. customThe resulting residue was purified by a silica gel column chromatography (eluant: 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-b600015882e74c5b8b35f77d223a157b
Source dataset
uspto-grants-1997_08
Patent number
US05658926

Reaction notes

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