4-[(4-Chlorophenyl)Sulfanyl]Benzonitrile → 1-{4-[(4-Chlorophenyl)sulfanyl]phenyl}methanamine

HRID 1792747Notes

Reaction equation

HRID 1792747 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 108793934-[(4-Chlorophenyl)Sulfanyl]BenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 220241851-{4-[(4-Chlorophenyl)sulfanyl]phenyl}methanamineYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chloro-phenylsulfanyl)-benzonitrile (4.91 g) in 100 mL of dry THF under nitrogen stirring at room temperature was added 40 mL of lithium aluminum hydride solution (1.0 M in THF) via syringe. The reaction mix was allowed to stir for 3.5 hours at room temperature, and was then heated to reflux for 4.5 hours, and then allowed to sit at room temperature overnight. The reaction mix was then cooled in an ice bath and quenched by addition of 10 mL water, followed by 1 mL of 15% aqueous NaOH solution and an additional 30 mL of water. Anhydrous sodium sulfate was added, and the mixture was filtered. The resulting filter cake was washed several times with Et2O. The combined ether filtrates were concentrated in vacuo to yield 4.67 g of 4-(4-chloro-phenylsulfanyl)-benzylamine as a white solid. MS M+H: 250.

Workup

  1. additionThe reaction mix
  2. temperaturewas then heated
  3. temperatureto reflux for 4.5 hours
  4. waitto sit at room temperature overnight
  5. additionThe reaction mix
  6. temperaturewas then cooled in an ice bath
  7. customquenched by addition of 10 mL water
  8. additionAnhydrous sodium sulfate was added
  9. filtrationthe mixture was filtered
  10. filtrationThe resulting filter cake
  11. washwas washed several times with Et2O
  12. concentrationThe combined ether filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-819fdb30593b4783b14fd368375a0969
Source dataset
uspto-grants-2006_07
Patent number
US07078401B2

Reaction notes

Loading…