Triethylamine → HCID 13727022, compound

HRID 1252165Notes

Reaction equation

HRID 1252165 reaction equation
[C:1]([CH2:4][C:5](=O)[CH3:6])(=O)[CH3:2].[CH3:8][C:9]1([CH3:21])[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([N:18]=[C:19]=[O:20])[C:12]=2[CH2:11][CH2:10]1.C(N(CC)CC)C.[CH2:29]([NH:31][NH2:32])C>C1(C)C=CC=CC=1.C(O)C>[CH3:29][N:31]1[C:1]([CH3:2])=[C:4]([C:19]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:12]=2[CH2:11][CH2:10][C:9]3([CH3:21])[CH3:8])=[O:20])[C:5]([CH3:6])=[N:32]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 29062EthylhydrazineHCID 31261AcetylacetoneHCID 13727020HCID 13727020, compound

Product 1

HCID 13727022HCID 13727022, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 600 mg (6.0 mmol) of acetylacetone and 1.12 g (6.0 mmol) of 1,1-dimethylindane-4-yl isocyanate in 10 ml of toluene was added dropwise 730 mg (7.2 mmol) of triethylamine at room temperature with stirring, followed by further stirring at room temperature for 12 hours. Then the reaction solution was concentrated under reduced pressure to obtain crude 3-(1,1-dimethylindane-4-yl carbamoyl)pentane-2,4-dione. Then, thus obtained crude 3-(1,1-dimethylindane-4-yl carbamoyl)pentane-2,4-dione was dissolved in 10 ml of ethanol. To the solution was added 276 mg (6.0 mmol) of ethylhydrazine, followed by stirring at room temperature for 6 hours and then for further one hour under reflux with heating. After left standing for cooling, the solvent was distilled off under reduced pressure and the residue was recrystallized with methanol to obtain 1.25 g of 1,3,5-trimethyl-N-(1,1-dimethylindane-4-yl)pyrazole-4-carboxamide which had a melting point of 151.6° C.

Workup

  1. stirringby further stirring at room temperature for 12 hours
  2. concentrationThen the reaction solution was concentrated under reduced pressure
  3. customto obtain crude 3-(1,1-dimethylindane-4-yl carbamoyl)pentane-2,4-dione
  4. customThen, thus obtained crude 3-(1,1-dimethylindane-4-yl carbamoyl)pentane-2,4-dione
  5. stirringby stirring at room temperature for 6 hours
  6. temperaturefor further one hour under reflux
  7. temperaturewith heating
  8. waitAfter left standing
  9. temperaturefor cooling
  10. distillationthe solvent was distilled off under reduced pressure
  11. customthe residue was recrystallized with methanol

Sources & evidence

ORD record
ord-9cc541f0374c4ae6b8f53da52d81e042
Source dataset
uspto-grants-1988_05
Patent number
US04742074

Reaction notes

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