Triethylamine → HCID 68840850, compound

HRID 490674Notes

Reaction equation

HRID 490674 reaction equation
[C:1]1([CH:7]2[CH2:11][NH:10][N:9]=[C:8]2[C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][S:19][C:20](=[N:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)(=[O:26])=[O:25])SC.C(N(CC)CC)C>C(#N)C>[CH3:18][S:19][C:20]([N:10]1[CH2:11][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:9]1)=[N:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)(=[O:25])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228333HCID 12228333, compoundHCID 17983255HCID 17983255, compound

Product 1

HCID 68840850HCID 68840850, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part C: Crude 4-phenyl-3-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole (9.81 g, 0.044 mol), [(4-chlorophenyl)sulfonyl]dithioimidocarbonic acid dimethyl ester (12.99 gram, 0.044 mol) and triethylamine (47 mL) are successively dissolved in acetonitrile. The resulting mixture is heated at reflux for 70 hours. The resulting mixture is allowed to attain room temperature and concentrated in vacuo. The residue is dissolved in dichloromethane. The organic layer is washed with water, dried over Na2SO4, filtered and concentrated in vacuo. Flash chromatographic purification (eluant: methanol/dichloromethane=5/95 (v/v)) gives N-((4-chlorophenyl)sulfonyl)-4-phenyl-3-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-1-carboximidothioic acid methyl ester (7.15 gram, 35% yield). ESI-MS (MH+) 471.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 70 hours
  3. customto attain room temperature
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue is dissolved in dichloromethane
  6. washThe organic layer is washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customFlash chromatographic purification (eluant: methanol/dichloromethane=5/95 (v/v))

Sources & evidence

ORD record
ord-6aced95ccbca4b3d8efd0c0757f72b1f
Source dataset
uspto-grants-2009_05
Patent number
US07528162B2

Reaction notes

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