Sodium Chloride → N-(2-Pyridinylmethyl)-N-[[4-(tetradecyloxy)phenyl]methyl]methanesulfonamide

HRID 1728888ノート

反応式

HRID 1728888 の反応式
[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].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:19][CH:18]=1.[Cl-].[Na+]>O1CCCC1>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:19][CH:18]=1)[S:11]([CH3:14])(=[O:13])=[O:12]

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 4657001N-(pyridin-2-ylmethyl)methanesulfonamideHCID 100228401-(Bromomethyl)-4-(tetradecyloxy)benzene

生成物 1

HCID 19014986N-(2-Pyridinylmethyl)-N-[[4-(tetradecyloxy)phenyl]methyl]methanesulfonamide収率 38.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a room temperature slurry of 0.391 g of 50% sodium hydride in 20 ml of dry tetrahydrofuran is added, via cannula, 1.27 g of product from Example 121 in 30 ml of dry tetrahydrofuran. The reaction is stirred at room temperature for 1.5 hours. Two and one half grams of product from Example 20 in 30 ml of dry tetrahydrofuran is added via cannula. The reaction is stirred at room temperature for 20 hours followed by heating at reflux temperature for 2 hours. The cooled reaction is poured into half saturated sodium chloride and extracted with methylene chloride. The combined organic layers are washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by chromatography (silica gel: 40% ethyl acetate/hexane) to give 1.22 g of the desired product as colorless crystals.

後処理

  1. stirringThe reaction is stirred at room temperature for 20 hours
  2. temperatureby heating
  3. temperatureat reflux temperature for 2 hours
  4. customThe cooled reaction
  5. extractionextracted with methylene chloride
  6. washThe combined organic layers are washed with saturated sodium chloride
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by chromatography (silica gel: 40% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-abeb253751d443a4ba7a9229a3cea3cb
出典データセット
uspto-grants-1994_07
特許番号
US05328921

反応ノート

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