4-Chlorophenyl Isocyanate → N,3-Bis(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide

HRID 978157Notes

Reaction equation

HRID 978157 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.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1>C(OCC)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([N:10]2[CH2:11][CH:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:9]2)=[O:28])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 113688843-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 173664N,3-Bis(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamideYield 88.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 500 ml round bottomed flask was suspended 55 g of 3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole in 250 ml of diethyl ether. The suspension was warmed to reflux and 33 g of 4-chlorophenyl isocyanate was added at a rate to maintain reflux. After cooling and standing overnight the precipitated product was filtered yielding 78 g of white solid. mp 173°-175° C.

Workup

  1. customIn a 500 ml round bottomed flask was suspended
  2. temperatureThe suspension was warmed
  3. temperatureto reflux
  4. temperatureto maintain
  5. temperaturereflux
  6. temperatureAfter cooling
  7. filtrationthe precipitated product was filtered

Sources & evidence

ORD record
ord-935c88bf5d344808b33d7497d128a1d5
Source dataset
uspto-grants-1987_05
Patent number
US04663341

Reaction notes

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