Sodium Chloride → N-(2-Pyridinylmethyl)-N-(methylsulfonyl)-4-(tetradecyloxy)benzamide

HRID 248025

반응식

HRID 248025 반응식
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12].[CH2:15]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[Cl-].[Na+]>O1CCCC1>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]([S:11]([CH3:14])(=[O:13])=[O:12])[C:34](=[O:35])[C:33]1[CH:32]=[CH:31][C:30]([O:29][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:38][CH:37]=1

참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 4657001N-(pyridin-2-ylmethyl)methanesulfonamideHCID 9998158Benzoyl chloride, 4-(tetradecyloxy)-

생성물 1

HCID 19014924N-(2-Pyridinylmethyl)-N-(methylsulfonyl)-4-(tetradecyloxy)benzamide수율 90.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a room temperature solution of 0.428 g of washed 50% sodium hydride in 15 ml of dry tetrahydrofuran is added, via cannula, 1.58 g of product from Example 121 dissolved in 20 ml of dry tetrahydrofuran. The mixture is stirred for 2 hours and 3.0 g of product from Example 3 dissolved in 20 ml of dry tetrahydrofuran is added, via cannula. After stirring at room temperature for 30 minutes, the reaction is heated at reflux temperature for 2 hours. The cooled mixture is poured into half saturated sodium chloride and extracted with chloroform. The organic layer is dried and concentrated in vacuo. The residue is purified by chromatography (silica gel: 15-40% ethyl acetate/hexane) to give 3.85 g of the desired product.

후처리

  1. additionis added, via cannula
  2. stirringAfter stirring at room temperature for 30 minutes
  3. temperaturethe reaction is heated
  4. temperatureat reflux temperature for 2 hours
  5. extractionextracted with chloroform
  6. customThe organic layer is dried
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by chromatography (silica gel: 15-40% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-d1044c7f8f5c471bb0204eee3a29fb07
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208247

연결된 노트

불러오는 중…