Acetic Acid → 1-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-one

HRID 2164698Notes

Reaction equation

HRID 2164698 reaction equation
[CH3:1][C:2]([CH3:12])([CH3:11])[C:3](=[O:10])[CH2:4][N:5]1[CH:9]=[N:8][CH:7]=[N:6]1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[C:4]([N:5]2[CH:9]=[N:8][CH:7]=[N:6]2)[C:3](=[O:10])[C:2]([CH3:12])([CH3:11])[CH3:1])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 8082PiperidineHCID 1008773,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone

Product 1

HCID 540228171-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-oneYield 12.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

167 g (1 mol) of 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one and 140.5 g (1 mol) of 4-chlorobenzaldehyde were dissolved in 700 ml of toluene and 1.2 g (0.02 mol) of glacial acetic acid and 1.8 ml (0.02 mol) of piperidine were added. The reaction mixture was heated for 40 hours to 120° C., while continuously separating off the water of reaction. Thereafter the reaction mixture was concentrated in vacuo and the oil which remained was distilled (boiling range 130°-160° C./0.04 mm Hg). The distillate was stirred with ethanol, whereupon crystals separated out. These were filtered off and dried. 35 g (12% of theory) of 1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-one (E isomer) of melting point 110° C. were thus obtained.

Workup

  1. temperatureThe reaction mixture was heated for 40 hours to 120° C.
  2. customwhile continuously separating off
  3. customthe water of reaction
  4. concentrationThereafter the reaction mixture was concentrated in vacuo
  5. distillationthe oil which remained was distilled (boiling range 130°-160° C./0.04 mm Hg)
  6. customseparated out
  7. filtrationThese were filtered off
  8. customdried

Sources & evidence

ORD record
ord-bc9d556fd0cf408a9fece3ee5634020f
Source dataset
uspto-grants-1985_03
Patent number
US04507141

Reaction notes

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