Acetic Acid → HCID 53942418, compound

HRID 1165701Notes

Reaction equation

HRID 1165701 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

210.5 g (1 mol) of 1-chloro-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-butan-3-one, 140.5 g (1 mol) of 4-chlorobenzaldehyde and 9.9 ml of piperidine and 30 g of glacial acetic acid were heated under reflux in 300 ml of toluene for 8 hours, the resulting water of reaction being removed azeotropically. The reaction mixture was thereafter washed with water and with dilute sodium bicarbonate solution, dried over sodium sulphate and concentrated in vacuo. 305.9 g (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 155° C./0.1 mm Hg were obtained as an E,Z isomer mixture. The E isomer could be isolated in crystalline form by stirring the isomer mixture with isopropanol or ethanol. It had a melting point of 112° C.

Workup

  1. custombeing removed azeotropically
  2. washThe reaction mixture was thereafter washed with water and with dilute sodium bicarbonate solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a8e9ad7ce694bc79ddce43e45144cab
Source dataset
uspto-grants-1990_03
Patent number
US04911750

Reaction notes

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