Potassium Carbonate → 4-(3-{Ethyl[3-(propylsulfanyl)propyl]amino}-2-hydroxypropoxy)benzonitrile

HRID 466219Notes

Reaction equation

HRID 466219 reaction equation
[CH2:1]([NH:3][CH2:4][CH:5]([OH:16])[CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)[CH3:2].Br[CH2:18][CH2:19][CH2:20][S:21][CH2:22][CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[CH2:1]([N:3]([CH2:18][CH2:19][CH2:20][S:21][CH2:22][CH2:23][CH3:24])[CH2:4][CH:5]([OH:16])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 150668414-[3-(Ethylamino)-2-hydroxypropoxy]-benzonitrileHCID 15158815HCID 15158815, compound

Product 1

HCID 150668434-(3-{Ethyl[3-(propylsulfanyl)propyl]amino}-2-hydroxypropoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4.7 g of 4-[3-(ethylamino)-2-hydroxypropoxy]-benzonitrile, 4.5 g of 1-bromo-3-(propylthio)-propane and 5.8 g potassium carbonate were mixed in 50 ml isopropanol and refluxed over night. The mixture was filtrated and evaporated. The residual oil 8.3 g was separated by column chromatography. Yield 4.9 g of the title compound.

Workup

  1. temperaturerefluxed over night
  2. filtrationThe mixture was filtrated
  3. customevaporated
  4. customThe residual oil 8.3 g was separated by column chromatography

Sources & evidence

ORD record
ord-3baa2f8ea9ef4245b312635fcc90b3bc
Source dataset
uspto-grants-1992_10
Patent number
US05155133

Reaction notes

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