2,2-Dimethyl-1,3-dioxane-4,6-dione → 2,2-Dimethyl-5-((thiophen-3-ylamino)methylene)-1,3-dioxane-4,6-dione

HRID 2359682Notes

Reaction equation

HRID 2359682 reaction equation
[C:1](O)(=O)C(O)=O.[NH2:7][C:8]1[CH:12]=[CH:11][S:10][CH:9]=1.C(OC(OCC)OCC)C.[CH3:23][C:24]1([CH3:32])[O:29][C:28](=[O:30])[CH2:27][C:26](=[O:31])[O:25]1>>[CH3:23][C:24]1([CH3:32])[O:29][C:28](=[O:30])[C:27](=[CH:1][NH:7][C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[C:26](=[O:31])[O:25]1

Participants

4

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformateHCID 22047570Thiophen-3-amine oxalate

Product 1

HCID 222500872,2-Dimethyl-5-((thiophen-3-ylamino)methylene)-1,3-dioxane-4,6-dioneYield 73.8%

Procedure

A 200-mL, rb flask equipped with a magnetic stirbar and a reflux condenser was charged with 3-aminothiophene oxalate (6.9 g, 36 mmol) and triethoxymethane (61 ml, 365 mmol) under N2. After stirring for 15 min, 2,2-dimethyl-1,3-dioxane-4,6-dione (5.3 g, 36 mmol) was added in one portion to the light brown slurry, and the mixture was heated to 85 deg C. in an oil bath overnight. The next day, a dark precipitate had formed and the mixture was cooled to ambient temp. The mixture was then cooled in an ice bath and the mixture was vacuum filtered through paper. The brown-red solids were washed with MTBE, air dried, then dried under vacuum to yield 2,2-dimethyl-5-((thiophen-3-ylamino)methylene)-1,3-dioxane-4,6-dione (6.73 g, 73% yield).

Workup

  1. customA 200-mL, rb flask equipped with a magnetic stirbar and a reflux condenser
  2. temperaturethe mixture was heated to 85 deg C
  3. customovernight
  4. customThe next day, a dark precipitate had formed
  5. temperatureThe mixture was then cooled in an ice bath
  6. filtrationfiltered through paper
  7. washThe brown-red solids were washed with MTBE, air
  8. customdried
  9. customdried under vacuum

Sources & evidence

ORD record
ord-d3efaff4032042adb56d994c91491ffe
Source dataset
uspto-grants-2014_04
Patent number
US08685983B2

Reaction notes

Loading…