Methyl iodide → HCID 18434022、化合物

HRID 1384857ノート

反応式

HRID 1384857 の反応式
[H-].[Na+].[CH2:3]([NH:6][C:7](=[S:18])[NH:8][C:9]1[S:10][CH:11]=[CH:12][C:13]=1[C:14]([O:16]C)=O)[CH2:4][CH3:5].[CH3:19]I>O1CCCC1>[CH3:19][S:18][C:7]1[N:6]([CH2:3][CH2:4][CH3:5])[C:14](=[O:16])[C:13]2[CH:12]=[CH:11][S:10][C:9]=2[N:8]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22966909HCID 22966909、化合物

生成物 1

HCID 18434022HCID 18434022、化合物収率 91.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

In a sulfonation flask, 2.9 g (0.072 mol) of a ca. 60% sodium hydride dispersion is added to 50 ml of absolute tetrahydrofurane. Then 17.7 g (0.069 mol) of methyl 2-(3-propylthioureido)thiophene-3-carboxylate, dissolved in 100 ml of absolute tetrahydrofurane, are added dropwise, such that the internal temperature remains constant at about 25° C. The mixture is stirred at reflux temperature for 5 hours and after cooling to room temperature 10.9 g (0.077 mol) of methyliodide, dissolved in 10 ml of tetrahydrofurane, are added dropwise. Then the mixture is stirred another 2 hours at reflux temperature. After completion of the reaction, the tetrahydrofurane is removed in the water-jet vacuum and the residue taken up in ethyl acetate. The organic layer is washed twice with water and then dried over sodium sulfate. After removal of the solvent in the water-jet vacuum, the crude product is obtained, which is purified by digestion in n-hexane. 15.1 g of 2-methylsulfanyl-3-propyl-3H-thieno[2.3-d]pyrimidin-4-one are obtained in the form of a slightly yellowish powder having a melting point of 94-96° C.

後処理

  1. additionare added dropwise, such that the internal temperature
  2. customremains constant at about 25° C
  3. temperatureat reflux temperature for 5 hours
  4. additionare added dropwise
  5. stirringThen the mixture is stirred another 2 hours
  6. temperatureat reflux temperature
  7. customAfter completion of the reaction
  8. customthe tetrahydrofurane is removed in the water-jet vacuum
  9. washThe organic layer is washed twice with water
  10. dry with materialdried over sodium sulfate
  11. customAfter removal of the solvent in the water-jet vacuum
  12. customthe crude product is obtained
  13. customwhich is purified by digestion in n-hexane

出典と根拠

ORDレコード
ord-7c3acba79a4a4a9c9e6c676ed5aa35c9
出典データセット
uspto-grants-2001_07
特許番号
US06262058B1

反応ノート

読み込み中…