Ethanol → 3-(4-Hydroxybutylsulfanyl)benzylamine

HRID 1985833Notes

Reaction equation

HRID 1985833 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20])(=O)C.C(O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.C(OCC)C.O>[OH:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH2:20]

Participants

8

Reactant 4

HCID 702EthanolHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 231438643-(4-Acetoxybutylsulfanyl)benzonitrile

Product 1

HCID 231438693-(4-Hydroxybutylsulfanyl)benzylamineYield 34.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Lithium aluminum hydride (0.20 g) was suspended in tetrahydrofuran (15 mL). To the mixture was added 3-(4-acetoxy-butylsulfanyl)benzonitrile (0.75 g) under ice-cooling. The mixture was stirred at 60° C. for 2 hours, and the mixture was cooled under ice-cooling. To the reaction mixture were added dropwise ethanol and water successively, and then added diethyl ether. To the reaction mixture was added anhydrous sodium sulfate, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure to give the title compound (0.22 g).

Workup

  1. temperaturecooling
  2. temperaturethe mixture was cooled under ice-
  3. temperaturecooling
  4. customthe insoluble material was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2125763121bf4254a05e3b1588a41eb4
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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