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Trimethyl orthoformate → 2,2-Dimethyl-5-[({4-[3-(methyloxy)phenyl]-2-thienyl}amino)methylidene]-1,3-dioxane-4,6-dione

HRID 573565
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HRID 573565 반응식
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH:11](OC)(OC)OC.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([C:26]2[CH:27]=[C:28]([NH2:31])[S:29][CH:30]=2)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[C:6](=[CH:11][NH:31][C:28]2[S:29][CH:30]=[C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH3:18])[CH:21]=3)[CH:27]=2)[C:4](=[O:5])[O:3]1
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참가 물질

5

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HCID 9005Trimethyl orthoformateHCID 11430Potassium CarbonateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 672362194-(3-Methoxyphenyl)thiophen-2-amine

생성물 1

HCID 672359842,2-Dimethyl-5-[({4-[3-(methyloxy)phenyl]-2-thienyl}amino)methylidene]-1,3-dioxane-4,6-dione수율 47.2%

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온도
110 °C

실험 절차

Meldrum's acid (1.58 g, 10.96 mmol) was dissolved in trimethyl orthoformate (24.23 mL, 219 mmol) and the mixture was heated at 110° C. for 1 h. After cooling to RT, 4-[3-(methyloxy)phenyl]-2-thiophenamine (Description 40) (1.5 g, 7.31 mmol) was added to the mixture and reheated at 90° C. for 15 h. After cooling to RT, the mixture was evaporated in vacuo. The residue was dissolved in DCM and treated with potassium carbonate (3.03 g, 21.92 mmol). After stirring for 30 min, the mixture was filtered and the filtrate was evaporated in vacuo, to give the title compound (1.24 g). LCMS (A) m/z: 360 [M+1]+, Rt 1.19 min (acidic).

후처리

  1. temperatureAfter cooling to RT
  2. temperatureAfter cooling to RT
  3. customthe mixture was evaporated in vacuo
  4. dissolutionThe residue was dissolved in DCM
  5. filtrationthe mixture was filtered
  6. customthe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-c1c37b9c54be475588cdb33f9232af08
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09029545B2

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