Acetic Acid → 1-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(2,4-dichlorophenyl)-propen-1-one

HRID 1164167Notes

Reaction equation

HRID 1164167 reaction equation
[CH3:1][C:2]1([C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH2:7][O:6][CH2:5][O:4][CH2:3]1.[Cl:16][C:17]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=1[CH:19]=O.N1CCCCC1.C(O)(=O)C>O.C1(C)C=CC=CC=1>[CH3:1][C:2]1([C:8](=[O:15])[C:9]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:19][C:18]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:17]=2[Cl:16])[CH2:7][O:6][CH2:5][O:4][CH2:3]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 134042,4-DichlorobenzaldehydeHCID 128556521-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one

Product 1

HCID 540933791-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(2,4-dichlorophenyl)-propen-1-oneYield 83.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 12.7 g (0.06 mole) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one, 10.8 g (0.06 mole) of 2,4-dichlorobenzaldehyde, 1 g of piperidine, 0.5 g of acetic acid and 150 ml of toluene is stirred for 10 hours under reflux, with elimination of water. The mixture is then cooled, washed with three times 80 ml of water, dried over sodium sulfate and concentrated under reduced pressure. The residue is dissolved in 250 ml of acetonitrile and the solution is decolorized with 1 g of animal charcoal at 40° C., concentrated to 40 ml and cooled to 0° C. The colorless precipitate is filtered off, washed with 40 ml of ether and dried. 18.4 g (83.3%) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(2,4-dichlorophenyl)-propen-1-one, of melting point 133°-135° C., are obtained.

Workup

  1. temperatureThe mixture is then cooled
  2. washwashed with three times 80 ml of water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue is dissolved in 250 ml of acetonitrile
  6. customis decolorized with 1 g of animal charcoal at 40° C.
  7. concentrationconcentrated to 40 ml
  8. filtrationThe colorless precipitate is filtered off
  9. washwashed with 40 ml of ether
  10. customdried

Sources & evidence

ORD record
ord-48d0e9019108483ca26921616dbdfe16
Source dataset
uspto-grants-1983_01
Patent number
US04368066

Reaction notes

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