(4-Chlorophenyl)hydrazine → 2-(4-chlorophenyl)-1,4-dihydro[1]benzothiopyrano[4,3-c]pyrazol-3(2H)-one

HRID 2286844Notes

Reaction equation

CO[C:3]([CH:5]1[C:14](=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[S:7][CH2:6]1)=[O:4].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[CH:19][CH:18]=1>C(O)(=O)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:3](=[O:4])[C:5]3[CH2:6][S:7][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[C:14]=3[NH:24]2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 115 °C

Procedure

4Oxo-3-thiochromancarboxylic acid methyl ester (10.4 g., 0.047 mole), [prepared by the method of Moriwake, J. Med. Chem. 9, 163 (1966)], was added to a round bottom flask containing p-chlorophenylhydrazine (7.4 g., 0.052 mole) and 3 ml. of glacial acetic acid. After stirring to obtain a homogeneous mixture, the reaction mixture was heated under nitrogen at an oil bath temperature of 115° C. The reaction mixture quickly liquefied and then turned to a yellow solid. Heating was continued at 115° C. for 20 minutes and the temperature then gradually raised to 180° C. and maintained there for about an hour. The reaction mixture was then cooled to room temperature, the solid was collected by filtration, washed with ether and dried. Recrystallization from isopropanol afforded product, m.p. 235° to 237° C. Weight: 10.3 g (70%).

Workup

addition9, 163 (1966)], was added to a round bottom flask
customto obtain a homogeneous mixture
temperatureHeating
temperaturethe temperature then gradually raised to 180° C.
temperaturemaintained there for about an hour
temperatureThe reaction mixture was then cooled to room temperature
filtrationthe solid was collected by filtration
washwashed with ether
customdried
customRecrystallization from isopropanol afforded product, m.p. 235° to 237° C

Sources & evidence

ORD record: ord-179e2ab71e804a728850365cd9fcb885
Source dataset: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04268516

Reaction notes

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