Dimethylformamide → 2-Amino-4-ethoxy-5-formylthiophene-3-carbonitrile

HRID 1591293ノート

反応式

HRID 1591293 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([O:9][CH2:10][CH3:11])[C:6]=1[C:7]#[N:8].[OH-].[Na+].CN(C)[CH:16]=[O:17]>P(Cl)(Cl)(Cl)=O>[NH2:1][C:2]1[S:3][C:4]([CH:16]=[O:17])=[C:5]([O:9][CH2:10][CH3:11])[C:6]=1[C:7]#[N:8]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 137423802-Amino-4-ethoxythiophene-3-carbonitrile

生成物 1

HCID 189632142-Amino-4-ethoxy-5-formylthiophene-3-carbonitrile

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

168 parts of 2-amino-3-cyano-4-ethoxythiophene (Example 1) are dissolved in 500 parts of dimethylformamide, and 200 parts of phosphoryl trichloride are added dropwise to the stirred solution. The reaction is exothermic, and the rate of dropwise addition is adjusted so that the temperature of the reaction mixture does not exceed 50° C. Stirring is continued for 4 hours at 50° C., 50 parts of ice are added, and the mixture is stirred until a clear solution has formed. This solution is run into 2000 parts of 12.5% strength sodium hydroxide solution and the temperature is kept at 20°-30° C. Stirring is continued for 8 hours at room temperature, after which the product is filtered off under suction, washed with water and dried. 185 parts of 2-amino-3-cyano-4-ethoxy-5-formylthiophene are obtained. A sample recrystallized from pentanol melts at 245°-246° C. and has the following analytical values:

後処理

  1. additionare added dropwise to the stirred solution
  2. additionthe rate of dropwise addition
  3. customdoes not exceed 50° C
  4. addition50 parts of ice are added
  5. stirringthe mixture is stirred until a clear solution
  6. customhas formed
  7. customis kept at 20°-30° C
  8. stirringStirring
  9. waitis continued for 8 hours at room temperature
  10. filtrationafter which the product is filtered off under suction
  11. washwashed with water
  12. customdried

出典と根拠

ORDレコード
ord-094d0e84c06c470da4ec7a13d279ac87
出典データセット
uspto-grants-1993_04
特許番号
US05206375

反応ノート

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