Dimethylamine → HCID 72758731, compound

HRID 1016603Notes

Reaction equation

HRID 1016603 reaction equation
CS[C:3]([N:15]1[CH2:19][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[N:16]1)=[N:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[CH3:33][NH:34][CH3:35].ClCCl>CO>[CH3:33][N:34]([CH3:35])[C:3]([N:15]1[CH2:19][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)=[N:16]1)=[N:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(=[O:6])=[O:7]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 6344DichloromethaneHCID 66791799HCID 66791799, compound

Product 1

HCID 72758731HCID 72758731, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Part B: To a stirred mixture of 3-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboximidothioic acid methyl ester (4.20 gram, 8.30 mmol) in methanol (75 ml) was added dimethylamine (10 ml) and dichloromethane (75 ml) and the resulting solution was stirred at room temperature for 6 hours. Evaporation in vacuo and subsequent flash chromatographic purification (diethyl ether/petroleum ether=1/1 (v/v), followed by diethyl ether) gave a solid which was further purified by recrystallisation from diisopropyl ether to yield N1,N1-dimethyl-N2-((4-chloro-phenyl)sulfonyl)-3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamidine (2.63 gram, 63% yield). Melting point: 182° C.

Workup

  1. customEvaporation
  2. customin vacuo and subsequent flash chromatographic purification (diethyl ether/petroleum ether=1/1 (v/v), followed by diethyl ether)
  3. customgave a solid which
  4. customwas further purified by recrystallisation from diisopropyl ether

Sources & evidence

ORD record
ord-cf8b3e1494d3401aa542326ffb6e8ddd
Source dataset
uspto-grants-2002_11
Patent number
US06476060B2

Reaction notes

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