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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
ノート
印刷プレビュー

反応式

HRID 573565 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

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

生成物 1

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

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c1c37b9c54be475588cdb33f9232af08
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09029545B2

反応ノート

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