Phenyl isocyanate → N-[4-(2-diethylaminoethoxy)phenyl]-N-[4,5-dihydro-1-phenyl-1H-pyrazol-3-yl]-N'-phenylurea

HRID 621595Notes

Reaction equation

HRID 621595 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([N:12]([CH2:34][CH3:35])[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:24]=2)=[CH:18][CH:17]=1)[CH3:11]>O1CCCC1>[CH2:34]([N:12]([CH2:10][CH3:11])[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]([C:23]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:24]=2)[C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:9])=[CH:20][CH:21]=1)[CH3:35]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 178464081HCID 178464081, compound

Product 1

HCID 22167070N-[4-(2-diethylaminoethoxy)phenyl]-N-[4,5-dihydro-1-phenyl-1H-pyrazol-3-yl]-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenylisocyanate (1.05 ml) was added dropwise to a solution of N-[4-(2-diethylaminoethoxy)phenyl]-4,5-dihydro-1-phenyl-1H-pyrazol-3-amine (2.4 g) in tetrahydrofuran (30 ml) and the solution heated to reflux for 4 hours. After cooling the solvent was removed and water added to the residue, which was then extracted with ether. The combined ether layer was washed with water and dried. Solvent was removed to give a solid which was recrystallised from ethyl acetate and petroleum ether to give the title compound (1.3 g) mp 140°-1°.

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling the solvent
  4. customwas removed
  5. additionwater added to the residue, which
  6. extractionwas then extracted with ether
  7. washThe combined ether layer was washed with water
  8. customdried
  9. customSolvent was removed
  10. customto give a solid which
  11. customwas recrystallised from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-14c60f16100e47dda195014341f77ff9
Source dataset
uspto-grants-1989_04
Patent number
US04824859

Reaction notes

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