Dimethylamine → HCID 22267386, compound

HRID 488711Notes

Reaction equation

HRID 488711 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][NH:17][N:16]=2)=[CH:11][CH:10]=1.[CH3:26][NH:27][CH3:28]>ClCCl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:19]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:18][N:17]([C:6]([NH:5][S:2]([N:27]([CH3:28])[CH3:26])(=[O:4])=[O:3])=[O:7])[N:16]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 70918Chlorosulfonyl isocyanateHCID 113688843-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 22267386HCID 22267386, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Part A: To a stirred solution of chlorosulfonyl isocyanate (1.73 mL, 20 mmol) in dry dichloromethane (20 mL) is very slowly added a solution of 3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole (5.13 gram, 20 mmol) in dry dichloromethane (125 mL) at −5° C. After stirring for 30 minutes the reaction mixture is allowed to attain room temperature and stirred for another 2 hours. After cooling to 0° C. liquid dimethylamine (5 mL) is added and the resulting solution is stirred for another hour at 0° C. and for 2 hours at room temperature. The solution is washed with water, filtered over hyflo and concentrated in vacuo. Flash chromatography (MTBE, Rf˜0.3) gives 3-(4-chlorophenyl)-N-((dimethylamino)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide (4.75 g, 58%). MP: 210-212° C.

Workup

  1. customto attain room temperature
  2. stirringstirred for another 2 hours
  3. additionis added
  4. stirringthe resulting solution is stirred for another hour at 0° C. and for 2 hours at room temperature
  5. washThe solution is washed with water
  6. filtrationfiltered over hyflo
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6269a6fe0d634d878decee242a4ec0c2
Source dataset
uspto-grants-2005_12
Patent number
US06974810B2

Reaction notes

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