Sodium Iodide → 2-[[3-[[3-(4-Cyanophenoxy)-2-hydroxypropyl]ethylamino]propyl]thio]benzamide

HRID 1087116Notes

Reaction equation

HRID 1087116 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH2:10])=[O:9].[CH2:15]([NH:17][CH2:18][CH:19]([OH:30])[CH2:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1)[CH3:16].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[C:26]([C:25]1[CH:28]=[CH:29][C:22]([O:21][CH2:20][CH:19]([OH:30])[CH2:18][N:17]([CH2:15][CH3:16])[CH2:2][CH2:3][CH2:4][S:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([NH2:10])=[O:9])=[CH:23][CH:24]=1)#[N:27]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 150668414-[3-(Ethylamino)-2-hydroxypropoxy]-benzonitrileHCID 151588182-(3-Chloropropylthio)benzamide

Product 1

HCID 151588192-[[3-[[3-(4-Cyanophenoxy)-2-hydroxypropyl]ethylamino]propyl]thio]benzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.5 g 2-(3- chloropropylthio)benzamide, 5.3 g of 4-[3-(ethylamino) -2-hydroxypropoxy]- benzonitrile, 6.6 g potassium carbonate and 7.2 g sodiumiodide were mixed in 100 ml of acetonitrile and heated to reflux for two days. The mixture was filtered and evaporated and the residue was dissolved in 1 M sulphuric acid. The acidic water layer was then washed twice with ether, alkalized with 10 M sodiumhydroxide and extracted with dichlormethane. The organic layer was dried over sodiumsulphate, treated with active carbon, filtered and evaporated. The residue, 8.7 g, was separated by column chromatography. Yield: 4.5 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for two days
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. dissolutionthe residue was dissolved in 1 M sulphuric acid
  6. washThe acidic water layer was then washed twice with ether
  7. extractionextracted with dichlormethane
  8. dry with materialThe organic layer was dried over sodiumsulphate
  9. additiontreated with active carbon
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue, 8.7 g, was separated by column chromatography

Sources & evidence

ORD record
ord-6ebdd1b9962f44d7b6f194ee28e645ab
Source dataset
uspto-grants-1991_07
Patent number
US05034411

Reaction notes

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