Triethylamine → HCID 20335426, compound

HRID 1706365Notes

Reaction equation

HRID 1706365 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[CH2:12][C:11]([CH3:15])=[N:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13](=[O:14])[CH:12]([C:31](=[O:32])[NH:30][C:27]3[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=3)[C:11]([CH3:15])=[N:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 709554-Fluorophenyl isocyanateHCID 1247322-(4-Methoxyphenyl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one

Product 1

HCID 20335426HCID 20335426, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the stirred suspension of 920 g of 1-(p-methoxyphenyl)-3-methyl-2-pyrazolin-5-one in 9,600 ml of toluene 460 g of triethylamine are added during 5 minutes, followed by 618 g of p-fluorophenylisocyanate. The mixture is stirred under nitrogen overnight at room temperature, cooled to 10° and combined with 5,000 ml of 1 N aqueous sodium hydroxide. The mixture is stirred for 15 minutes, the organic phase separated and extracted twice with 2,000 ml of 1 N aqueous sodium hydroxide again. The combined aqueous solutions are washed twice with 2,000 ml of diethyl ether each, cooled to 5° and acidified with 900 ml of concentrated hydrochloride acid during 30 minutes. The resulting suspension is stirred for 1 hour, filtered and the residue washed 6 times with 2,000 ml of water each. 1,364 g thereof are dissolved in 55,000 ml of boiling ethanol, the solution filtered hot and the filtrate stirred under nitrogen overnight at room temperature. The precipitate formed is filtered off, washed twice with 1,000 ml of cold ethanol each and recrystallized from ethanol again, to yield the 1-(p-methoxyphenyl)-3-methyl-4-(p-fluorophenylcarbamoyl)-2-pyrazolin-5-one melting at 255°-257° with decomposition; it is identical with that obtained according to Example 6.

Workup

  1. additionare added during 5 minutes
  2. temperaturecooled to 10°
  3. stirringThe mixture is stirred for 15 minutes
  4. customthe organic phase separated
  5. extractionextracted twice with 2,000 ml of 1 N aqueous sodium hydroxide again
  6. washThe combined aqueous solutions are washed twice with 2,000 ml of diethyl ether each,
  7. temperaturecooled to 5°
  8. waitacidified with 900 ml of concentrated hydrochloride acid during 30 minutes
  9. stirringThe resulting suspension is stirred for 1 hour
  10. filtrationfiltered
  11. washthe residue washed 6 times with 2,000 ml of water each
  12. dissolution1,364 g thereof are dissolved in 55,000 ml of boiling ethanol
  13. filtrationthe solution filtered hot
  14. stirringthe filtrate stirred under nitrogen overnight at room temperature
  15. customThe precipitate formed
  16. filtrationis filtered off
  17. washwashed twice with 1,000 ml of cold ethanol each and
  18. customrecrystallized from ethanol again

Sources & evidence

ORD record
ord-0d6574f5a19941a095363561eb45e424
Source dataset
uspto-grants-1980_06
Patent number
US04207317

Reaction notes

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