N,N-Diethylaniline → HCID 13727024, compound

HRID 1252167Notes

Reaction equation

HRID 1252167 reaction equation
[CH3:1][N:2]1[C:6](=O)[CH:5]([C:8]([NH:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][CH2:14][C:15]3([CH3:21])[CH3:20])=[O:9])[C:4]([CH3:22])=[N:3]1.P(Cl)(Cl)([Cl:25])=O.C(N(CC)C1C=CC=CC=1)C>>[Cl:25][C:6]1[N:2]([CH3:1])[N:3]=[C:4]([CH3:22])[C:5]=1[C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][CH2:14][C:15]2([CH3:21])[CH3:20])=[O:9]

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 13852006HCID 13852006, compound

Product 1

HCID 13727024HCID 13727024, compound

Procedure

1.12 g (10 mmol) of 1,3-dimethylpyrazoline-5-one was suspended in 10 ml of toluene containing 1.11 g of triethylamine. To the suspension was added dropwise a solution of 1.87 g of 1,1-dimethylindane-4-yl isocyanate in 2 ml of toluene with stirring at room temperature, followed by further stirring at room temperature for 12 hours. Thereafter, the reaction mixture was extracted with water three times. The aqueous layers were made acidic with concentrated hydrochloric acid and cooled with ice. The precipitate produced was filtered and air-dried to obtain 1.81 g of 1,3-dimethyl-5-oxo-N-(1,1-dimethylindane-4-yl)4,5-dihydropyrazole-4-carboxamide (mp 141.4° C.). Then, thus obtained 1,3-dimethyl-5-oxo-N-(1,1-dimethylindane-4-yl)-4,5-dihydropyrazole-4-carboxamide was added to a mixture of 5 ml of phosphorus oxychloride and 907 mg of N,N-diethylaniline. The resultant mixture was stirred under reflux with heating for 1.5 hour. The obtained reaction mixture was poured into ice water and extracted with chloroform three times. The chloroform layer was washed with water and dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure and the residue was recrystallized with ethanol to obtain 0.96 g of 5-chloro-1,3-dimethyl-N-(1,1-dimethylindane-4-yl)pyrazole-4-carboxamide (mp 175.2° C.).

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 1.5 hour
  3. customThe obtained reaction mixture
  4. extractionextracted with chloroform three times
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThereafter, the solvent was distilled off under reduced pressure
  8. customthe residue was recrystallized with ethanol

Sources & evidence

ORD record
ord-42cff6600af247dfb6d5794c053191c4
Source dataset
uspto-grants-1988_05
Patent number
US04742074

Reaction notes

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