3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole → HCID 22267339, compound

HRID 1822119Notes

Reaction equation

HRID 1822119 reaction equation
[N:1]1([S:7]([N:10]=[C:11]=[S:12])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:23][NH:22][N:21]=2)=[CH:16][CH:15]=1>ClCCl>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:23][N:22]([C:11](=[S:12])[NH:10][S:7]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)(=[O:9])=[O:8])[N:21]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 113688843-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazoleHCID 22267352HCID 22267352, compound

Product 1

HCID 22267339HCID 22267339, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Part A: To a stirred solution of (piperidin-1-yl)sulfonyl isothiocyanate (54.77 g, 266 mmol) in dry dichloromethane (900 mL) in a nitrogen atmosphere is added 3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole (68.3 gram, 266 mmol). After stirring for 16 hours an additional amount of dichloromethane is added. The resulting solution is twice washed with water, dried over Na2SO4, and concentrated in vacuo. After addition of MTBE, the residue crystallizes. The crystalline material is collected and washed with MTBE to give 3-(4-chlorophenyl)-4-phenyl-N-((piperidin-1-yl)sulfonyl)-4,5-dihydro-1H-pyrazole-1-thiocarboxamide (77.6 gram, 63% yield).

Workup

  1. additionis added
  2. washThe resulting solution is twice washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. additionAfter addition of MTBE
  6. customthe residue crystallizes
  7. customThe crystalline material is collected
  8. washwashed with MTBE

Sources & evidence

ORD record
ord-0d6cc3da313e4fbd9e22b9e2691a3a57
Source dataset
uspto-grants-2009_10
Patent number
US07608718B2

Reaction notes

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