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

HRID 2266354ノート

反応式

HRID 2266354 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8970036260234e8c807e84cdd1e85470
出典データセット
uspto-grants-2010_12
特許番号
US07858623B2

反応ノート

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