Benzene → 1-Phenyl-3-methyl-4-(p-methylthiophenylcarbamoyl)-2-pyrazolin-5-one

HRID 1706362Notes

Reaction equation

HRID 1706362 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH2:10][C:9]([CH3:13])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC=CC=1.[CH3:20][S:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1>C(N(CC)CC)C>[C:1]1([N:7]2[C:11](=[O:12])[CH:10]([C:29](=[O:30])[NH:28][C:25]3[CH:26]=[CH:27][C:22]([S:21][CH3:20])=[CH:23][CH:24]=3)[C:9]([CH3:13])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 4021Mci-186HCID 27333164-(Methylthio)phenyl isocyanate

Product 1

HCID 203354271-Phenyl-3-methyl-4-(p-methylthiophenylcarbamoyl)-2-pyrazolin-5-one

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The mixture of 2.6 g of 1-phenyl-3-methyl-2-pyrazolin-5-one, 75 ml of benzene, 1.8 g of triethylamine and 2.5 g of p-methylthiophenylisocyanate is stirred at ambient temperature and allowed to stand overnight. It is evaporated; the residue taken up in methanol, the solution is filtered and combined with the mixture of 10 ml of 5 N hydrochloric acid and 250 ml of water. The precipitate formed is collected, washed with water, dried, triturated with diethyl ether and dissolved in 2 N aqueous sodium hydroxide. The solution is filtered, acidified with 5 N hydrochloric acid, the precipitate washed with water, dried, triturated with methanol and recrystallized from ethyl acetate, to yield the 1-phenyl-3-methyl-4-(p-methylthiophenylcarbamoyl)-2-pyrazolin-5-one melting at 196°-199°.

Workup

  1. customIt is evaporated
  2. filtrationthe solution is filtered
  3. additioncombined with the mixture of 10 ml of 5 N hydrochloric acid and 250 ml of water
  4. customThe precipitate formed
  5. customis collected
  6. washwashed with water
  7. customdried
  8. customtriturated with diethyl ether
  9. dissolutiondissolved in 2 N aqueous sodium hydroxide
  10. filtrationThe solution is filtered
  11. washthe precipitate washed with water
  12. customdried
  13. customtriturated with methanol
  14. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a12e771c55984f629a3c92ddb227b09e
Source dataset
uspto-grants-1980_06
Patent number
US04207317

Reaction notes

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