Water → [3-Methyl-4-(methylsulfanyl)phenyl]methanamine

HRID 527373Notes

Reaction equation

HRID 527373 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[S:16][CH3:17])[C:11]#[N:12].O.[OH-].[Na+]>C1COCC1>[CH3:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[S:16][CH3:17])[CH2:11][NH2:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 578566063-Methyl-4-(methylsulfanyl)benzonitrile

Product 1

HCID 61023193[3-Methyl-4-(methylsulfanyl)phenyl]methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminium hydride (1.0 M in THF, 18.4 mL, 18.4 mmol) is cooled in an ice bath and treated slowly with a solution of 3-methyl-4-methylsulfanyl-benzonitrile (preparation 66a, 1.0 g, 6.1 mmol) in THF (10 mL) while the temperature is kept below 5° C. The mixture is allowed to warm to room temperature and stirred over night. The mixture is cooled again at 0° C., and water (2 mL) and aqueous sodium hydroxide (4 M, 2 mL) is added. The mixture is filtered and the filtrate is extracted twice with dichloromethane. The combined organic layers are concentrated under reduced pressure. Yield: 923 mg (90% of theory); ESI mass spectrum: [M+H−NH3]+=151; r.t. HPLC: 0.61 min (X011_S03).

Workup

  1. customis kept below 5° C
  2. temperatureThe mixture is cooled again at 0° C.
  3. filtrationThe mixture is filtered
  4. extractionthe filtrate is extracted twice with dichloromethane
  5. concentrationThe combined organic layers are concentrated under reduced pressure
  6. customr.t
  7. custom0.61 min (X011_S03)

Sources & evidence

ORD record
ord-f77b3ce070fc45589cefa66fd7f0f85e
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

Loading…