3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole → 3-(4-chlorophenyl)-N-(((ethyl)propyl-amino)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-thiocarboxamide

HRID 488710Notes

Reaction equation

HRID 488710 reaction equation
[CH2:1]([N:3]([CH2:10][CH2:11][CH3:12])[S:4]([N:7]=[C:8]=[S:9])(=[O:6])=[O:5])[CH3:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:23][NH:22][N:21]=2)=[CH:16][CH:15]=1>ClCCl>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:23][N:22]([C:8](=[S:9])[NH:7][S:4]([N:3]([CH2:1][CH3:2])[CH2:10][CH2:11][CH3:12])(=[O:6])=[O:5])[N:21]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 113688843-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazoleHCID 11469850((Ethyl)propylamino)sulfonyl isothiocyanate

Product 1

HCID 113747113-(4-chlorophenyl)-N-(((ethyl)propyl-amino)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-thiocarboxamideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part A: To a stirred solution of ((ethyl)propylamino)sulfonyl isothiocyanate (5.98 gram, 25.4 mmol) in dry dichloromethane in a nitrogen atmosphere is added of 3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole (6.52 gram, 25.4 mmol). After stirring for 90 minutes the resulting solution is concentrated in vacuo and purified by column chromatography (CH2Cl2, silicagel, Rf˜0.45). The resulting solid is recrystallized from diethyl ether to give 3-(4-chlorophenyl)-N-(((ethyl)propylamino)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-thiocarboxamide (6.57 gram, 56% yield). Melting point: 144-146° C.

Workup

  1. concentrationis concentrated in vacuo
  2. custompurified by column chromatography (CH2Cl2, silicagel, Rf˜0.45)
  3. customThe resulting solid is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-b974c505996147cf88bf867cebfe3fb6
Source dataset
uspto-grants-2005_12
Patent number
US06974810B2

Reaction notes

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