Pyridine → 3-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4-phenyl4,5-dihydro-1H-pyrazole-1-carboxamide

HRID 1016604Notes

Reaction equation

HRID 1016604 reaction equation
CO[C:3](=[O:15])[NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].N1C=CC=CC=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:32][NH:31][N:30]=2)=[CH:25][CH:24]=1>O1CCOCC1>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:33]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:32][N:31]([C:3]([NH:4][S:5]([C:8]3[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=3)(=[O:6])=[O:7])=[O:15])[N:30]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 5013687Methyl (4-chlorophenyl)sulfonylcarbamateHCID 113688843-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 113748943-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4-phenyl4,5-dihydro-1H-pyrazole-1-carboxamideYield 83.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Part A: To a solution of N-((4-chlorophenyl)sulfonyl)carbamic acid methyl ester (CAS: 34543-04-9) (2.99 gram, 12.0 mmol) and pyridine (4 ml) in 1,4-dioxane (20 ml) was added 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (3.39 gram, 13.2 mmol) and the resulting mixture was stirred for 4 hours at 100° C. After concentration in vacuo the residue was dissolved in dichloromethane, successively washed with water, 1 N HCl and water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to a volume of 20 ml. Methyl-tert-butyl ether (60 ml) was added and the resulting solution was concentrated to a volume of 20 ml. The formed crystals were collected by filtration and recrystallised from methyl-tert-butyl ether to give 3-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide (4.75 gram, 76% yield). Melting point: 211-214° C.

Workup

  1. concentrationAfter concentration in vacuo the residue
  2. dissolutionwas dissolved in dichloromethane
  3. washsuccessively washed with water, 1 N HCl and water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a volume of 20 ml
  7. additionMethyl-tert-butyl ether (60 ml) was added
  8. concentrationthe resulting solution was concentrated to a volume of 20 ml
  9. filtrationThe formed crystals were collected by filtration
  10. customrecrystallised from methyl-tert-butyl ether

Sources & evidence

ORD record
ord-0fde4bf5b2244b4580ef22aba542466e
Source dataset
uspto-grants-2002_11
Patent number
US06476060B2

Reaction notes

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