2,2,6-Trimethyl-4H-1,3-dioxin-4-one → HCID 13745283, compound

HRID 649305Notes

Reaction equation

HRID 649305 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12](=[O:20])[CH2:13][C:14](=NN(C)C)[CH3:15])[CH3:2].CC1(C)[O:27][C:26](=O)[CH:25]=[C:24]([CH3:29])[O:23]1>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:13]1[C:26](=[O:27])[CH:25]=[C:24]([CH3:29])[O:23][C:14]=1[CH3:15])=[O:20])[CH3:2]

Participants

4

Reactant 2

HCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-oneHCID 53780352N-(2,6-Diethylphenyl)-3-(dimethylhydrazinylidene)butanamide

Product 1

HCID 13745283HCID 13745283, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 25.0 g (90.8 m mol) of N-(2,6-diethylphenyl)-3-(N,N-dimethylhydrazono)butyramide and 130 ml of toluene was refluxed, to which a solution of 28.4 g (200 m mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one was dropwise added over a period of 30 minutes. The mixture was further refluxed for 2 hours. After distilling off the solvent, 200 ml of ethyl ether was added to the residue. The mixture was well stirred and filtered to remove insoluble material. The filtrate was concentrated and subjected to chromatography to remove high polar impurities. The resultant product was recrystallized from hexane to obtain 20.2 g (Yield 74%) of the title compound.

Workup

  1. additionwas dropwise added over a period of 30 minutes
  2. temperatureThe mixture was further refluxed for 2 hours
  3. distillationAfter distilling off the solvent, 200 ml of ethyl ether
  4. additionwas added to the residue
  5. filtrationfiltered
  6. customto remove insoluble material
  7. concentrationThe filtrate was concentrated
  8. customto remove high polar impurities
  9. customThe resultant product was recrystallized from hexane

Sources & evidence

ORD record
ord-4b129cc43418489eafaea84ff844a8dc
Source dataset
uspto-grants-1988_04
Patent number
US04739083

Reaction notes

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