Acetic Acid → [3-Bromo-5-(4-nitro-phenylsulphanyl)-phenyl]-ethylmethylamine

HRID 1603627Notes

Reaction equation

HRID 1603627 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:18][CH3:19])[CH:5]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH:7]=1.[CH:20](=O)[CH3:21].[BH3-]C#N.[Na+].C(O)(=O)C>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([N:18]([CH2:20][CH3:21])[CH3:19])[CH:5]=[C:6]([S:8][C:9]2[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 19605547[3-Bromo-5-(4-nitrophenylsulphanyl)-phenyl]-methylamine

Product 1

HCID 53691384[3-Bromo-5-(4-nitro-phenylsulphanyl)-phenyl]-ethylmethylamineYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.34 g (0.001 mol) of [3-bromo-5-(4-nitrophenylsulphanyl)-phenyl]-methylamine was dissolved in 10 ml of acetonitrile, treated with 1.4 ml (0.025 mol) of acetaldehyde, 0.74 g (0.010 mol) of NaBH3CN and 1.76 ml of acetic acid and stirred at room temperature for 1 hr. Thereafter, the solvent was removed, the residue was partitioned in ethyl acetate/water and the organic phase was washed with sat. sodium chloride solution, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:19. There was obtained 0.33 g (93%) of [3-bromo-5-(4-nitro-phenylsulphanyl)-phenyl]-ethylmethylamine as an orange-red oil. MS (EI): me/e=368, 366 (C15H15BrN2O2S+).

Workup

  1. customThereafter, the solvent was removed
  2. customthe residue was partitioned in ethyl acetate/water
  3. washthe organic phase was washed with sat. sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel with ethyl acetate/hexane 1:19

Sources & evidence

ORD record
ord-a4c938cdf46743d894f854d042f10d11
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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