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

HRID 1031951Notes

Reaction equation

HRID 1031951 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-e182dbdf1ef8449dad3f0f622cf63da2
Source dataset
uspto-grants-1990_09
Patent number
US04956378

Reaction notes

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