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Water → N-(2-butyl-3-((4-(3-(dibutylamino)propoxy)phenyl)(hydroxy)methyl)benzofuran-5-yl)methanesulfonamide

HRID 1048913
ノート
印刷プレビュー

反応式

HRID 1048913 の反応式
[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4].[CH2:19]([N:23]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=[O:33])=[CH:30][CH:29]=1)[CH2:20][CH2:21][CH3:22].O>FC(F)(F)C(O)=O>[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])=[CH:10][C:8]=2[C:9]=1[CH:32]([C:31]1[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH2:25][CH2:24][N:23]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:35][CH:34]=1)[OH:33])[CH2:2][CH2:3][CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 9878493N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamideHCID 141464004-(3-Dibutylamino-propoxy)-benzaldehyde

生成物 1

HCID 19754447N-(2-butyl-3-((4-(3-(dibutylamino)propoxy)phenyl)(hydroxy)methyl)benzofuran-5-yl)methanesulfonamide収率 33%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
40 °C

実験手順

5.34 g of N-(2-butyl-1-benzofuran-5-yl)methanesulfonamide (II) (0.02 mol, 1 eq) is dissolved in 40 mL of trifluoroacetic acid and 8.7 g of 4-(3-dibutylamino-propoxy)-benzaldehyde (V) (0.03 mol, 1.5 eq) is added to the solution. The reaction mixture is heated to 40° C. and stirred for 10 hours at this temperature. The mixture is cooled to room temperature and 100 mL of water is added. After 15 min of stirring, the product is extracted with 2×50 mL of dichloromethane. The organic phase is concentrated and the crude product is purified by column chromatography (spheric silica; eluent:toluene:MTBE:methanol=50:40:10) to obtain 3.68 g of compound (VI) (33%).

後処理

  1. temperatureThe mixture is cooled to room temperature
  2. stirringAfter 15 min of stirring
  3. extractionthe product is extracted with 2×50 mL of dichloromethane
  4. concentrationThe organic phase is concentrated
  5. customthe crude product is purified by column chromatography (spheric silica; eluent:toluene:MTBE:methanol=50:40:10)

出典と根拠

ORDレコード
ord-6cefae166ca44e3a9495b594ccea4b03
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09382223B2

反応ノート

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