Sodium Iodide → 4-[3-[Ethyl[3-(phenylthio) propyl]amino]-2-hydroxypropoxy]-benzonitrile

HRID 1087113Notes

Reaction equation

HRID 1087113 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].Cl[CH2:18][CH2:19][CH2:20][S:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH2:1]([N:3]([CH2:18][CH2:19][CH2:20][S:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[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

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2696063-Chloropropyl phenyl sulfideHCID 150668414-[3-(Ethylamino)-2-hydroxypropoxy]-benzonitrile

Product 1

HCID 151588134-[3-[Ethyl[3-(phenylthio) propyl]amino]-2-hydroxypropoxy]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.0 g of 4-[3-(ethylamino)-2-hydroxypropoxy]-benzonitrile and 4.0 g of 1-chloro-3-(phenylthio) propane was dissolved in 70 ml of acetonitrile and mixed with 6.4 g potassium carbonate and 8.0 g of sodium iodide. The mixture was refluxed over night, filtrated, evaporated and the residue was dissolved in 2 M hydrochloric acid. This acidic waterlayer was washed with two portions of diethylether, alkalized with 10 M sodium hydroxide and extracted with three portions of dichlorometane. The combined layers of dichloromethane were dried over sodium sulphate and evaporated. The oily residue was purified by column chromatography on silica gel. Yield: 2.1 g of the title compound.

Workup

  1. temperatureThe mixture was refluxed over night
  2. filtrationfiltrated
  3. customevaporated
  4. dissolutionthe residue was dissolved in 2 M hydrochloric acid
  5. washThis acidic waterlayer was washed with two portions of diethylether
  6. extractionextracted with three portions of dichlorometane
  7. dry with materialThe combined layers of dichloromethane were dried over sodium sulphate
  8. customevaporated
  9. customThe oily residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bf82bb9fe8d34ba0a569d0bd55d8b34a
Source dataset
uspto-grants-1991_07
Patent number
US05034411

Reaction notes

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