Methanol → 1-Acetamido-2-amino-4-methoxymethylthiobenzene

HRID 616123Notes

Reaction equation

HRID 616123 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][O:13][CH3:14])=[CH:7][C:6]=1[N+:15]([O-])=O)(=[O:3])[CH3:2].CO>[Fe].O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][O:13][CH3:14])=[CH:7][C:6]=1[NH2:15])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 20362834N-{4-[(Methoxymethyl)sulfanyl]-2-nitrophenyl}acetamide

Product 1

HCID 203712101-Acetamido-2-amino-4-methoxymethylthiobenzene

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

1.5 G. of 1-acetamido-2-nitro-4-methoxymethylthiobenzene, also prepared according to Example VIII, is treated for 4 hours in a refluxing mixture of 160 ml. methanol and 40 ml. water with 4 g. of iron powder (added in two portions) and 1 g. ferrous sulfate. The mixture is filtered, and the filtrate concentrated. The residue is dissolved in chloroform and washed with water, then the solvent evaporated to afford 1-acetamido-2-amino-4-methoxymethylthiobenzene.

Workup

  1. additionis treated for 4 hours in a refluxing mixture of 160 ml
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate concentrated
  4. dissolutionThe residue is dissolved in chloroform
  5. washwashed with water
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-1473cd785d6147daabf5b222ab171057
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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