Triethylamine → HCID 20335441, compound

HRID 1706364Notes

Reaction equation

HRID 1706364 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.[F:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=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:30](=[O:31])[NH:29][C:26]3[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=3)[C:10]([CH3:14])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709554-Fluorophenyl isocyanateHCID 830553H-Pyrazol-3-one, 2-(4-chlorophenyl)-2,4-dihydro-5-methyl-

Product 1

HCID 20335441HCID 20335441, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The suspension of 3.1 g of 1-(p-chlorophenyl)-3-methyl-2-pyrazolin-5-one in 100 ml of benzene is treated with 1.8 g of triethylamine, warmed until dissolution and combined with 2.1 g of p-fluorophenylisocyanate while stirring. After standing overnight at room temperature it is evaporated, the residue taken up in methanol and the solution treated with the mixture of 10 ml of 5 N hydrochloric acid and 250 ml of water. The mixture is extracted with ethyl acetate, the extract washed with water, dried and evaporated. The crude solid is dissolved in 2 N aqueous sodium hydroxide, the solution filtered and acidified with 5 N hydrochloric acid. The precipitate is collected, washed with water and recrystallized from ethyl acetate-petroleum ether, to yield the 1-(p-chlorophenyl)-3-methyl-4-(p-fluorophenylcarbamoyl)-2-pyrazolin-5-one melting at 240°-242° with decomposition.

Workup

  1. temperaturewarmed until dissolution
  2. customit is evaporated
  3. additionthe solution treated with the mixture of 10 ml of 5 N hydrochloric acid and 250 ml of water
  4. extractionThe mixture is extracted with ethyl acetate
  5. washthe extract washed with water
  6. customdried
  7. customevaporated
  8. dissolutionThe crude solid is dissolved in 2 N aqueous sodium hydroxide
  9. filtrationthe solution filtered
  10. customThe precipitate is collected
  11. washwashed with water
  12. customrecrystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-24dc7e3c03134c1cb6be316926c00e2b
Source dataset
uspto-grants-1980_06
Patent number
US04207317

Reaction notes

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