Diisopropylethylamine → HCID 25055669, compound

HRID 1666194Notes

Reaction equation

HRID 1666194 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[N:12]=[C:11]([CH2:22][NH2:23])[CH2:10]2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[Cl:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[C:35]=1[S:41](Cl)(=[O:43])=[O:42]>ClCCl>[Cl:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[C:35]=1[S:41]([NH:23][CH2:22][C:11]1[CH2:10][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=2)[N:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[N:12]=1)(=[O:42])=[O:43]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 157253702-Chloro-6-methylbenzene-1-sulfonyl chlorideHCID 44224963HCID 44224963, compound

Product 1

HCID 25055669HCID 25055669, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-yl]methyl amine hydrochloride (391 mg, 1 mmol) was suspended in dry dichloromethane (10 mL), and diisopropylethylamine (323 mg, 0.25 mmol) was added. The reaction mixture was stirred at room temperature for 15 min. 2-Chloro-6-methyl-benzenesulfonyl chloride (225 mg, 1 mmol) was added and the reaction mixture was stirred at room temperature overnight. The solution was then washed with water, dried over anhydrous sodium sulfate and the solvent evaporated under reduced pressure to yield 2-chloro-N-[5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-ylmethyl]-6-methyl-benzenesulfonamide which was purified by column chromatography using dichloromethane/methanol (98:2) (440 mg, 81% as a cream solid).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. washThe solution was then washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-69de76a3d542485b99bdd916cb30cd50
Source dataset
uspto-grants-2011_10
Patent number
US08044053B2

Reaction notes

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