3-(Dimethylamino)-2-[3-(trifluoromethyl)phenyl]prop-2-enal → 1-(2-Hydroxybutyl)-4-(m-trifluoromethylphenyl)-pyrazole

HRID 1973423Notes

Reaction equation

HRID 1973423 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9](=[CH:12]N(C)C)[CH:10]=O)[CH:6]=[CH:7][CH:8]=1.[OH:18][CH:19]([CH2:23][CH3:24])[CH2:20][NH:21][NH2:22]>C1C=CC=CC=1>[OH:18][CH:19]([CH2:23][CH3:24])[CH2:20][N:21]1[CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:17])[F:16])[CH:4]=2)[CH:12]=[N:22]1

Participants

4

Reactant 2

HCID 37090863-(Dimethylamino)-2-[3-(trifluoromethyl)phenyl]prop-2-enalHCID 41131272-Hydroxybutylhydrazine

Product 1

HCID 214915151-(2-Hydroxybutyl)-4-(m-trifluoromethylphenyl)-pyrazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 10 g. of 2-(m-trifluoromethylphenyl)-3-dimethylaminoacrolein, 5 g. of 2-hydroxybutylhydrazine and 100 ml. of benzene is refluxed for 2.5 hours. The benzene is evaporated off, ether added, and the reaction mixture cooled to obtain a precipitate which is recovered by filtering, washed with pentane, dissolved in methylene chloride, dried, treated with charcoal and filtered. The resulting solution is treated by addition of pentane and the resulting precipitate recovered by filtering, washed with pentane and dried under reduced pressure to obtain 1-(2-hydroxybutyl)-4-(m-trifluoromethylphenyl)-pyrazole, m.p. 77°-79°C.

Workup

  1. additionA mixture of 10 g
  2. customThe benzene is evaporated off
  3. additionether added
  4. temperaturethe reaction mixture cooled
  5. customto obtain a precipitate which
  6. customis recovered
  7. filtrationby filtering
  8. washwashed with pentane
  9. dissolutiondissolved in methylene chloride
  10. customdried
  11. additiontreated with charcoal
  12. filtrationfiltered
  13. additionThe resulting solution is treated by addition of pentane
  14. customthe resulting precipitate recovered
  15. filtrationby filtering
  16. washwashed with pentane
  17. customdried under reduced pressure

Sources & evidence

ORD record
ord-6993e45d70424c79aed0e971f28cdfc6
Source dataset
uspto-grants-1976_12
Patent number
US03997555

Reaction notes

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