Methyl Thioglycolate → Methyl 3-amino-4-phenylthiophene-2-carboxylate

HRID 1775602

反応式

HRID 1775602 の反応式
CO[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:5]#[N:6].C[O-].[Na+].[C:16]([O:20][CH3:21])(=[O:19])[CH2:17][SH:18]>>[NH2:6][C:5]1[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:3][S:18][C:17]=1[C:16]([O:20][CH3:21])=[O:19]

参加物

4

反応物 3

HCID 16907Methyl ThioglycolateHCID 10942334Sodium MethoxideHCID 545703493-Methoxy-2-phenylacrylonitrile

生成物 1

HCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylate収率 26%

反応条件

温度
65 °C

実験手順

3-Methoxy-2-phenylacrylonitrile (17.9 g, 112.5 mmol) was dissolved in NaOMe (5 M in MeOH, 31.5 ml, 157.5 mmol), and then methyl thioglycolate (16 ml, 180.0 mmol) was added thereto. The mixture was heated with stirring at 65° C. for 24 hr. After the completion of the reaction was confirmed by thin layer chromatography (TLC), the reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was washed with distilled water and extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was distilled under reduced pressure, and the concentrate was purified by silica gel column chromatography (EtOAc:Hex=1:5) to give 5.1 g (21.9 mmol, 26% yield in three steps) of the title compound.

後処理

  1. temperatureThe mixture was heated
  2. temperaturethe reaction mixture was cooled to room temperature
  3. filtrationfiltered through Celite
  4. washThe filtrate was washed with distilled water
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. distillationThe filtrate was distilled under reduced pressure
  9. customthe concentrate was purified by silica gel column chromatography (EtOAc:Hex=1:5)

出典と根拠

ORDレコード
ord-7b527c2a61394df98de362b0cf7a98af
出典データセット
uspto-grants-2016_02
特許番号
US09260448B2

関連ノート

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