Triethylamine → HCID 66791799, compound

HRID 1016602Notes

Reaction equation

HRID 1016602 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:19][S:20][C:21](=[N:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])SC.C(N(CC)CC)C>C(#N)C>[CH3:19][S:20][C:21]([N:10]1[CH2:11][CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:9]1)=[N:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)(=[O:26])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 113688843-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole2×HCID 12228333HCID 12228333, compound

Product 1

HCID 66791799HCID 66791799, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part A: A stirred mixture of 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (12.0 gram, 46.8 mmol), [(4-chlorophenyl)sulfonyl]dithioimidocarbonic acid dimethyl ester (CAS: 13068-12-7) (9.20 gram, 31.1 mmol) and triethylamine (15 ml) in acetonitrile (200 ml) was heated at reflux temperature for 20 hours. An additional portion of 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (12.0 gram, 46.8 mmol) was added and the resulting mixture was heated at reflux temperature for another 16 hours. After concentration in vacuo, dichloromethane was added and the resulting solution was washed twice with water and dried over anhydrous Na2SO4. After filtration and evaporation in vacuo the residue was further purified by flash chromatography (diethyl ether/petroleum ether=1/1 (v/v)) to give 3-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboximidothioic acid methyl ester (12.5 gram, 80% yield based on [(4-chlorophenyl)sulfonyl]dithioimidocarbonic acid dimethyl ester) as an amorphous solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 20 hours
  3. temperaturethe resulting mixture was heated
  4. temperatureat reflux temperature for another 16 hours
  5. concentrationAfter concentration in vacuo, dichloromethane
  6. additionwas added
  7. washthe resulting solution was washed twice with water
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationAfter filtration and evaporation in vacuo the residue
  10. customwas further purified by flash chromatography (diethyl ether/petroleum ether=1/1 (v/v))

Sources & evidence

ORD record
ord-82adff16f0b54ca5b3ca43d2b7b8a4f0
Source dataset
uspto-grants-2002_11
Patent number
US06476060B2

Reaction notes

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