Methanol → 2-n-Butyl-3-[4-(2-diethylaminoethoxy)phenylsulfonyl]benzofuran

HRID 1764662Notes

Reaction equation

HRID 1764662 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=2[C:9]=1[S:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:2][CH2:3][CH3:4].CO.[Na].[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31]Cl)[CH3:28]>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[O:6][C:7]2[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=2[C:9]=1[S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:28][CH2:27][N:29]([CH2:33][CH3:34])[CH2:30][CH3:31])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 13364Diethylaminoethyl chlorideHCID 5360545SodiumHCID 149563642-n-Butyl-3-(4-hydroxyphenylsulfonyl)benzofuran

Product 1

HCID 197591262-n-Butyl-3-[4-(2-diethylaminoethoxy)phenylsulfonyl]benzofuran

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1.4 g. (0.0042 mol.) of 2-n-butyl-3-(4-hydroxyphenylsulfonyl)benzofuran in 20 ml. of methanol was added 25 ml. of methanol containing 110 mg. (0.0048 g.-atom) of sodium. The reaction mixture was heated on a steam bath for 30 minutes then evaporated to dryness. The residue was dissolved in 25 ml. of toluene and ca. 1 ml. of methanol, a suspension of 0.615 g. (0.0048 mol.) of distilled 2-diethylaminoethyl chloride in 15 ml. of toluene was added and the resulting mixture was heated on a steam bath for 3 hours. The solution was filtered through MgSO4 and chromatographed on silica gel with 50:50 ether-acetone to give the title compound.

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for 30 minutes
  2. customthen evaporated to dryness
  3. dissolutionThe residue was dissolved in 25 ml
  4. additionof methanol, a suspension of 0.615 g
  5. temperaturethe resulting mixture was heated on a steam bath for 3 hours
  6. filtrationThe solution was filtered through MgSO4
  7. customchromatographed on silica gel with 50:50 ether-acetone

Sources & evidence

ORD record
ord-d5d99ab4c1214e81b2f3b03e5f627bff
Source dataset
uspto-grants-1978_09
Patent number
US04117128

Reaction notes

Loading…