Acetic Acid → HCID 53942418, compound

HRID 568749Notes

Reaction equation

HRID 568749 reaction equation
[Cl:1][CH2:2][C:3]([CH3:13])([CH3:12])[C:4](=[O:11])[CH2:5][N:6]1[CH:10]=[N:9][CH:8]=[N:7]1.[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[Cl:1][CH2:2][C:3]([CH3:13])([CH3:12])[C:4](=[O:11])[C:5]([N:6]1[CH:10]=[N:9][CH:8]=[N:7]1)=[CH:19][C:18]1[CH:21]=[CH:22][C:15]([Cl:14])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 8082PiperidineHCID 12849946HCID 12849946, compound

Product 1

HCID 53942418HCID 53942418, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

201.5 g (1 mole) of 1-chloro-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-butan-3-one, 140.5 g (1 mole) of 4-chlorobenzaldehyde, 9,9 ml of piperidine and 30 g of glacial acetic acid in 300 ml of toluene were heated under reflux for 8 hours, the water of reaction formed being removed azeotropically. The reaction mixture was then washed with water and with dilute sodium bicarbonate solution, dried over sodium sulphate and evaporated in vacuo. 305.9 (94.4% of theory) of crude 1-chloro-5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-4-penten-3-one of boiling point 165° C./0.1 mm Hg were obtained as the E/Z-isomer mixture. The E-isomer could be isolated as crystals by stirring the product with isopropanol or ethanol. The E-isomer had a melting point of 112° C.

Workup

  1. temperatureunder reflux for 8 hours
  2. customformed
  3. custombeing removed azeotropically
  4. washThe reaction mixture was then washed with water and with dilute sodium bicarbonate solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ef164be3906e469e9a778f19b29c28ed
Source dataset
uspto-grants-1988_03
Patent number
US04729783

Reaction notes

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