Sodium Dithionite → 4-Methoxy-3-methylsulfanylmethyl-phenylamine

HRID 47440Notes

Reaction equation

HRID 47440 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=1[CH2:20][S:21][CH3:22].C(=O)([O-])O.[Na+]>CO.O>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=1[CH2:20][S:21][CH3:22]

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 227451381-Methoxy-2-methylsulfanylmethyl-4-nitrobenzene

Product 1

HCID 227451794-Methoxy-3-methylsulfanylmethyl-phenylamineYield 33.5%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Sodium dithionite (3.264 g) was added to a solution of 1-methoxy-2-methylsulfanylmethyl-4-nitro-benzene (0.8 g), and sodium hydrogen carbonate (1.57 g) in methanol:water (1:1, 200 ml) and stirred at room temperature for 16 h. Solvent was removed at reduced pressure, the residue partitioned between water and ethyl acetate, the organic phase separated, washed with brine dried (Na2SO4) and solvent removed at reduced pressure to give the title compound (0.23 g) as a brown oil. m/z (API+): 184 (MH+).

Workup

  1. customSolvent was removed at reduced pressure
  2. customthe residue partitioned between water and ethyl acetate
  3. customthe organic phase separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4) and solvent
  6. customremoved at reduced pressure

Sources & evidence

ORD record
ord-7eb1f9319b0a402c825caf499aa87c8f
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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