5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 2,2-Dimethyl-5-[(3-oxo-5-phenyl-1-cyclohexenylamino)methylene]-[1,3]dioxane-4,6-dione

HRID 1700504Notes

Reaction equation

HRID 1700504 reaction equation
CO[CH:3]=[C:4]1[C:9](=[O:10])[O:8][C:7]([CH3:12])([CH3:11])[O:6][C:5]1=[O:13].[NH2:14][C:15]1[CH2:20][CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:18][C:17](=[O:27])[CH:16]=1>C(#N)C>[CH3:12][C:7]1([CH3:11])[O:6][C:5](=[O:13])[C:4](=[CH:3][NH:14][C:15]2[CH2:20][CH:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:18][C:17](=[O:27])[CH:16]=2)[C:9](=[O:10])[O:8]1

Participants

4

Reactant 2

HCID 1521115-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 122101053-Amino-5-phenyl-2-cyclohexen-1-one

Product 1

HCID 183175972,2-Dimethyl-5-[(3-oxo-5-phenyl-1-cyclohexenylamino)methylene]-[1,3]dioxane-4,6-dioneYield 36.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-methoxymethylene-2,2-dimethyl-[1,3]dioxane-4,6-dione (1.8 g) in acetonitrile (15 ml) was added 1-amino-5-phenylcyclohexen-3-one (2.0 g), and the mixture was stirred at room temperature for 24 hours. The resulting crystals were filtered and washed with acetonitrile to give crystals of 2,2-dimethyl-5-[(3-oxo-5-phenyl-1-cyclohexenylamino)methylene]-[1,3]dioxane-4,6-dione (1.2 g).

Workup

  1. filtrationThe resulting crystals were filtered
  2. washwashed with acetonitrile

Sources & evidence

ORD record
ord-cdce752347b749f1805f078f8f03185f
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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