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Carbon Disulfide → 6-(3-Isothiocyanatopropoxy)carbostyril

HRID 2257901
Notes
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Reaction equation

HRID 2257901 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2.[C:18](=S)=[S:19].[OH-].[Na+].C(Cl)(=O)OCC>O>[N:2]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2)=[C:18]=[S:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 114141486-(3-aminopropoxy)-1H-quinolin-2-one;hydrochloride

Product 1

HCID 229236916-(3-Isothiocyanatopropoxy)carbostyrilYield 21.4%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
80 °C

Procedure

1.28 g of 6-(3-aminopropoxy)carbostyril hydrochloride was added, at 0° C., to 10 ml of an aqueous solution containing 0.3 g of carbon disulfide and 0.4 g of sodium hydroxide. The mixture was stirred at 80° C. for about 2 hours. Thereto was added 0.55 g of ethyl chlorocarbonate at 35° C. The resulting mixture was stirred for 30 minutes. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The filtrate was dried with magnesium sulfate. The solvent was removed by distillation. To the resulting residue was added diethyl ether, and the resulting crystals were collected by filtration and purified by a silica gel column chromatography (eluant: 3.3% methanol/dichloromethane) to obtain 0.22 g of 6-(3-isothiocyanatopropoxy)carbostyril.

Workup

  1. stirringThe resulting mixture was stirred for 30 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe filtrate was dried with magnesium sulfate
  4. customThe solvent was removed by distillation
  5. additionTo the resulting residue was added diethyl ether
  6. filtrationthe resulting crystals were collected by filtration
  7. custompurified by a silica gel column chromatography (eluant: 3.3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-5330a9fa9cdf4aefb3d4a8d43ebf7875
Source dataset
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05658926

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes