Triethylamine → HCID 13852006, compound

HRID 1252166Notes

Reaction equation

HRID 1252166 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH:5]=[C:4]([CH3:8])[NH:3]1.C(N(CC)CC)C.[CH3:16][C:17]1([CH3:29])[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([N:26]=[C:27]=[O:28])[C:20]=2[CH2:19][CH2:18]1>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:6](=[O:7])[CH:5]([C:27]([NH:26][C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:20]=2[CH2:19][CH2:18][C:17]3([CH3:29])[CH3:16])=[O:28])[C:4]([CH3:8])=[N:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27668471,3-dimethyl-1H-pyrazol-5-olHCID 13727020HCID 13727020, compound

Product 1

HCID 13852006HCID 13852006, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

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. stirringby further stirring at room temperature for 12 hours
  2. extractionThereafter, the reaction mixture was extracted with water three times
  3. temperaturecooled with ice
  4. customThe precipitate produced
  5. filtrationwas filtered
  6. customair-dried

Sources & evidence

ORD record
ord-fe7bdf6d077441779b27550cac1428e8
Source dataset
uspto-grants-1988_05
Patent number
US04742074

Reaction notes

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