5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione → Methyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-methoxybenzoate

HRID 393663

Reaction equation

HRID 393663 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])[NH2:6].[CH3:14][C:15]1([CH3:26])[O:20][C:19](=[O:21])[C:18](=[CH:22]OC)[C:17](=[O:25])[O:16]1>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])[NH:6][CH:22]=[C:18]1[C:17](=[O:25])[O:16][C:15]([CH3:14])([CH3:26])[O:20][C:19]1=[O:21]

Participants

4

Reactant 2

HCID 1521115-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 168705Methyl 4-amino-o-anisate

Product 1

HCID 22646557Methyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-methoxybenzoateYield 96.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

3-Methoxy-4-methoxycarbonylaniline (14.15 g, 78 mmol) was suspended in isopropanol and heated at 50° C. 2,2-Dimethyl-5-methoxymethylene-1,3-dioxane-4,6-dione (14.8 g, 80 mmol), (Montatsh. Chem. 1967, 98, 564), was then added in portions over 10 minutes and the mixture was heated at reflux for 30 minutes. The mixture was left to cool to ambient temperature overnight. The precipitate formed was collected by filtration, washed with isopropanol and dried under vacuum to give 5-((3-methoxy-4-methoxycarbonylanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (25.2 g, 96%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. waitThe mixture was left
  4. temperatureto cool to ambient temperature overnight
  5. customThe precipitate formed
  6. filtrationwas collected by filtration
  7. washwashed with isopropanol
  8. customdried under vacuum

Sources & evidence

ORD record
ord-9924ef78b0284c45b6b40f18e00b8704
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Linked notes

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