Methanol → 4-[(Methoxymethyl)sulfanyl]benzene-1,2-diamine

HRID 596587Notes

Reaction equation

HRID 596587 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9]COC)=[CH:4][C:3]=1[N+:13]([O-])=O.[CH3:16][OH:17]>[Fe].O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][O:17][CH3:16])=[CH:4][C:3]=1[NH2:13]

Participants

5

Reactant 2

HCID 887MethanolHCID 539497771-Amino-2-nitro-4-methoxyethylthiobenzene

Product 1

HCID 203628324-[(Methoxymethyl)sulfanyl]benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

1.3 G. of 1-amino-2-nitro-4-methoxyethylthiobenzene is treated in 80 ml. methanol and 20 ml. water at reflux under nitrogen, with 0.7 g. ferrous sulfate and 2.8 g. iron (added in two portions) for 4 hours. The mixture is filtered, stripped under vacuum, and the residue recrystallized from cyclohexane. 1,2-Diamino-4-methoxymethylthiobenzene is thus obtained.

Workup

  1. filtrationThe mixture is filtered
  2. customthe residue recrystallized from cyclohexane

Sources & evidence

ORD record
ord-4dbc6b2a5ce7412ea4e7daf9d4a2acc0
Source dataset
uspto-grants-1977_03
Patent number
US04011320

Reaction notes

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