Carbon Disulfide → 6-(3-Isothiocyanatopropoxy)carbostyril

HRID 2257901Notes

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]

Participants

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

stirringThe resulting mixture was stirred for 30 minutes
extractionfollowed by extraction with ethyl acetate
dry with materialThe filtrate was dried with magnesium sulfate
customThe solvent was removed by distillation
additionTo the resulting residue was added diethyl ether
filtrationthe resulting crystals were collected by filtration
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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