3-Dimethylamino-3'-trifluoromethylacrylophenone → HCID 11198195, compound

HRID 225299Notes

Reaction equation

HRID 225299 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH2:7][C:8]#[N:9])[C:3]=1[C:10]#[N:11].CN(C)[CH:14]=[CH:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)=O>C(O)(=O)C>[C:10]([C:3]1[C:4]([CH2:7][C:8]#[N:9])=[N:5][N:6]2[C:16]([C:18]3[CH:19]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:21]=[CH:22][CH:23]=3)=[CH:15][CH:14]=[N:1][C:2]=12)#[N:11]

Participants

4

Reactant 2

HCID 7300243-Dimethylamino-3'-trifluoromethylacrylophenoneHCID 178510900HCID 178510900, compound

Product 1

HCID 11198195HCID 11198195, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.94 g. of 5-amino-4-cyano-3-cyanomethyl pyrazole and 4.86 g. of 3-dimethylamino-3'-trifluoromethylacrylophenone in 25 ml. of glacial acetic acid is refluxed for 16 hours. The reaction mixture is evaporated to dryness and then extracted with methylene chloride. This solution is washed with a saturated sodium bicarbonate solution and dried with sodium sulfate. After passage of this solution through a short column of hydrous magnesium silicate, the effluent from this column is refluxed with gradual addition of hexane until the product crystallizes. Filtration gives crystals, m.p. 180°-181° C.

Workup

  1. additionA mixture of 2.94 g
  2. customThe reaction mixture is evaporated to dryness
  3. extractionextracted with methylene chloride
  4. washThis solution is washed with a saturated sodium bicarbonate solution
  5. dry with materialdried with sodium sulfate
  6. temperatureAfter passage of this solution through a short column of hydrous magnesium silicate, the effluent from this column is refluxed with gradual addition of hexane until the product
  7. customcrystallizes
  8. filtrationFiltration
  9. customgives crystals, m.p. 180°-181° C.

Sources & evidence

ORD record
ord-639ffcade5a5448d860a514b39f4dd00
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Reaction notes

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