Hydrochloric Acid → 2-(4-chlorophenyl)-N'-(4-fluorophenyl)sulfonyl-3-phenyl-3,4-dihydropyrazole-5-carboximidamide

HRID 19760Notes

Reaction equation

HRID 19760 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][C:10]([C:19]([NH2:21])=[NH:20])=[N:9]2)=[CH:4][CH:3]=1.Cl.[F:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(#N)C>[F:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:20][C:19]([C:10]2[CH2:11][CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]=2)=[NH:21])(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 116594121-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamidine

Product 1

HCID 1785134592-(4-chlorophenyl)-N'-(4-fluorophenyl)sulfonyl-3-phenyl-3,4-dihydropyrazole-5-carboximidamideYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part B: To a stirred solution of 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamidine.HCl (1.87 gram, 5 mmol) and 4-fluorophenylsulfonyl chloride (0.97 g, 5 mmol) in anhydrous acetonitrile (20 ml) is added triethylamine (2.1 ml, 15 mmol) and the resulting mixture is stirred at room temperature for 16 hours. After concentration in vacuo, the residue is dissolved in a mixture of Ethyl acetate and water. The Ethyl acetate layer is collected, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue is recrystallised from methyl-t-butyl ether to give N-[(4-fluorophenyl)sulfonyl]-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamidine (1.22 gram, 54% yield). Melting point: 200-203.5° C.

Workup

  1. concentrationAfter concentration in vacuo
  2. dissolutionthe residue is dissolved in a mixture of Ethyl acetate and water
  3. customThe Ethyl acetate layer is collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue is recrystallised from methyl-t-butyl ether

Sources & evidence

ORD record
ord-a069822636bd4ee6823d7935e6bad9f4
Source dataset
uspto-grants-2010_06
Patent number
US07745476B2

Reaction notes

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