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

HRID 1048913Notes

Reaction equation

HRID 1048913 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
40 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-6cefae166ca44e3a9495b594ccea4b03
Source dataset
uspto-grants-2016_07
Patent number
US09382223B2

Reaction notes

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