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

HRID 1048912Notes

Reaction equation

HRID 1048912 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].[Li]CCCC.CCCCCC.[CH2:30]([N:34]([CH2:47][CH2:48][CH2:49][CH3:50])[CH2:35][CH2:36][CH2:37][O:38][C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[O:44])=[CH:41][CH:40]=1)[CH2:31][CH2:32][CH3:33].[NH4+].[Cl-]>CCCCCC.C1COCC1>[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:43]([C:42]1[CH:41]=[CH:40][C:39]([O:38][CH2:37][CH2:36][CH2:35][N:34]([CH2:47][CH2:48][CH2:49][CH3:50])[CH2:30][CH2:31][CH2:32][CH3:33])=[CH:46][CH:45]=1)[OH:44])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 9878493N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamideHCID 141464004-(3-Dibutylamino-propoxy)-benzaldehydeHCID 178418244HCID 178418244, compound

Product 1

HCID 19754447N-(2-butyl-3-((4-(3-(dibutylamino)propoxy)phenyl)(hydroxy)methyl)benzofuran-5-yl)methanesulfonamideYield 40.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

2.67 g of N-(2-butyl-1-benzofuran-5-yl)methanesulfonamide (II) (0.01 mol, 1 eq) is dissolved in 35 mL of n-hexane and 7 mL of 2.5 M BuLi hexane solution is added in 30 min during which the temperature is kept at 20° C. The reaction mixture is stirred for 2 hours at room temperature and then it is added to the solution of 4.37 g of 4-(3-dibutylamino-propoxy)-benzaldehyde (V) (0.015 mol, 1.5 eq) in 80 mL of THF. The reaction mixture is stirred at room temperature for 2 hours and then 40 mL of NH4Cl solution is added. After 15 min of stirring, the product is extracted with 2×40 mL of diethyl ether. 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 2.24 g of compound (VI) (40%).

Workup

  1. customis kept at 20° C
  2. stirringThe reaction mixture is stirred at room temperature for 2 hours
  3. stirringAfter 15 min of stirring
  4. extractionthe product is extracted with 2×40 mL of diethyl ether
  5. concentrationThe organic phase is concentrated
  6. customthe crude product is purified by column chromatography (spheric silica; eluent:toluene:MTBE:methanol=50:40:10)

Sources & evidence

ORD record
ord-e9a7294c2bf64434a1975fc52485112e
Source dataset
uspto-grants-2016_07
Patent number
US09382223B2

Reaction notes

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