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

HRID 1607208Notes

Reaction equation

HRID 1607208 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([CH3:13])[CH2:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1>C(Cl)Cl>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:10]2[CH2:11][CH:12]([CH3:13])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:9]2)=[O:23])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 137525563-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 13752557N,3-bis-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 500 ml round bottomed flask was placed 82 g (0.42 mole) of 3-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole dissolved in 300 ml of methylene chloride and the solution was brought to boiling. A solution of 64.5 g of 4-chlorophenyl isocyanate (0.42 mole) in 100 ml of methylene chloride was added at a rate to maintain reflux. After stirring for an additional 30 minutes the solvent was removed in vacuo and the resulting oil was crystallized from ethyl ether yielding 140 g of N,3-bis-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide. mp 139°-140° C. NMR data was consistent with the structure.

Workup

  1. customIn a 500 ml round bottomed flask was placed
  2. temperatureto maintain
  3. temperaturereflux
  4. customwas removed in vacuo
  5. customthe resulting oil was crystallized from ethyl ether yielding 140 g of N,3-bis-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

Sources & evidence

ORD record
ord-e164f841d8d44d7a9934a04af5938ee1
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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