Potassium Carbonate → 4-[2-[Ethyl[3-(propylthio)propyl]amino]-1-hydroxyethyl]-benzonitrile

HRID 1087114Notes

Reaction equation

HRID 1087114 reaction equation
[CH2:1]([NH:3][CH2:4][CH:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)[OH:6])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27][CH3:28]>C(#N)C>[CH2:1]([N:3]([CH2:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27][CH3:28])[CH2:4][CH:5]([C:7]1[CH:8]=[CH:9][C:10]([C:11]#[N:12])=[CH:13][CH:14]=1)[OH:6])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 151588144-[2-(Ethylamino)-1-hydroxyethyl]-benzonitrileHCID 15158815HCID 15158815, compound

Product 1

HCID 151588164-[2-[Ethyl[3-(propylthio)propyl]amino]-1-hydroxyethyl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.5 g of 4-[2-(ethylamino)-1-hydroxyethyl]-benzonitrile, 2.1 g of potassiumcarbonate, 1.7 g of 1-bromo-3-(propylthio)-propane was mixed in 50 ml acetonitrile and refluxed over night. The mixture was filtered and evaporated and the residue was dissolved in 2 M hydrochloric acid. The acidic waterlayer was washed twice with ether, alkalized with 10 M sodiumhydroxide and extracted with three portions of dichloromethane.

Workup

  1. temperaturerefluxed over night
  2. filtrationThe mixture was filtered
  3. customevaporated
  4. dissolutionthe residue was dissolved in 2 M hydrochloric acid
  5. washThe acidic waterlayer was washed twice with ether
  6. extractionextracted with three portions of dichloromethane

Sources & evidence

ORD record
ord-04cf098f4ce6497cb848cf0e61953b78
Source dataset
uspto-grants-1991_07
Patent number
US05034411

Reaction notes

Loading…