Methanol → 4-[(Methylsulfanyl)methoxy]benzene-1,2-diamine

HRID 1679465Notes

Reaction equation

HRID 1679465 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([O:11][CH2:12][S:13][CH3:14])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.CO>[Fe].C(O)(=O)C>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([O:11][CH2:12][S:13][CH3:14])=[CH:10][C:4]=1[NH2:1]

Participants

5

Reactant 2

HCID 887MethanolHCID 203628264-[(Methylsulfanyl)methoxy]-2-nitroaniline

Product 1

HCID 203628424-[(Methylsulfanyl)methoxy]benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

4.5 G. of 2-nitro-4-methylthiomethoxyaniline in 95 ml. of methanol and 5 ml. of acetic acid is treated with 8 g. of iron powder and the mixture is refluxed for 4 hours. The hot solution is filtered and the solvent evaporated. The residue is treated with hot tetrahydrofuran. The mixture is filtered and the solvent evaporated to give 1,2-diamino-4-methylthiomethoxybenzene.

Workup

  1. filtrationThe hot solution is filtered
  2. customthe solvent evaporated
  3. additionThe residue is treated with hot tetrahydrofuran
  4. filtrationThe mixture is filtered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-5de3f546c55245bab41ca3c5aa60ad3b
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

Loading…