Diisopropylethylamine → 3-(4-chlorophenyl)-1-[3-((4-chlorophenyl)sulfonyl)butanoyl]-4,5-dihydro-4-phenyl-1H-pyrazole

HRID 1016605Notes

Reaction equation

HRID 1016605 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([CH3:16])[CH2:12][C:13]([OH:15])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C.[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:49]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[CH2:48][NH:47][N:46]=2)=[CH:41][CH:40]=1>>[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]2[CH:49]([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH2:48][N:47]([C:13](=[O:15])[CH2:12][CH:11]([S:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)(=[O:9])=[O:10])[CH3:16])[N:46]=2)=[CH:43][CH:44]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27390873-(4-Chlorobenzenesulfonyl)butyric acidHCID 113688843-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 112142203-(4-chlorophenyl)-1-[3-((4-chlorophenyl)sulfonyl)butanoyl]-4,5-dihydro-4-phenyl-1H-pyrazoleYield 105.1%

Procedure

To a stirred mixture of 3-((4-chlorophenyl)sulfonyl)butyric acid (1.85 gram, 7.00 mmol), diisopropylethylamine (3 ml) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.50 gram, 15.7 mmol) was added 3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole (3.00 gram, 11.7 mmol) and the resulting mixture was stirred for 16 hours at room temperature. After concentration in vacuo the resulting residue was purified by flash chromatography (petroleum ether/diethyl ether=1/2 (v/v), followed by diethyl ether) to give 3-(4-chlorophenyl)-1-[3-((4-chlorophenyl)sulfonyl)butanoyl]-4,5-dihydro-4-phenyl-1H-pyrazole (3.69 gram, 63% yield) as a diastereomeric mixture. Melting point: amorphous.

Workup

  1. concentrationAfter concentration in vacuo the resulting residue
  2. customwas purified by flash chromatography (petroleum ether/diethyl ether=1/2 (v/v), followed by diethyl ether)

Sources & evidence

ORD record
ord-350e7035b7824fe79ec65675a03c6aa1
Source dataset
uspto-grants-2002_11
Patent number
US06476060B2

Reaction notes

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