Phenyl isocyanate → HCID 20335435, compound

HRID 1706354Notes

Reaction equation

HRID 1706354 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH2:11][C:10]([CH3:14])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12](=[O:13])[CH:11]([C:29](=[O:30])[NH:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:10]([CH3:14])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 830553H-Pyrazol-3-one, 2-(4-chlorophenyl)-2,4-dihydro-5-methyl-

Product 1

HCID 20335435HCID 20335435, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The stirred suspension of 4.2 g of 1-(p-chlorophenyl)-3-methyl-2-pyrazolin-5-one in 100 ml of benzene is gently warmed with 2.4 g of triethylamine until all solid is dissolved. The deep red solution is combined with 2.4 g of phenylisocyanate, and after 2 hours' standing at ambient temperature, a lower layer is present. The mixture is evaporated, the residue taken up in 0.3 N hydrochloric acid and the mixture extracted with ethyl acetate. The extract is washed with water, dried, evaporated, the residue is triturated with diethyl ether and recrystallized from methanol to yield the 1-(p-chlorophenyl)-3-methyl-4-phenylcarbamoyl-2-pyrazolin-5-one of Formula II with R'=R"=H and R=Cl, melting at 212°-215° (dec.).

Workup

  1. dissolutionis dissolved
  2. customThe mixture is evaporated
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. customevaporated
  7. customthe residue is triturated with diethyl ether
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-41c2f30519f74bd8b6611737fd8d7829
Source dataset
uspto-grants-1980_06
Patent number
US04207317

Reaction notes

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