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

HRID 415897노트

반응식

HRID 415897 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3e1a2f5162254540ab97deee333c2511
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088794B2

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