Sodium Hydroxide → 4-[(Methylsulfanyl)methoxy]-2-nitroaniline

HRID 1414780Notes

Reaction equation

HRID 1414780 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][S:13][CH3:14])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])(=O)C.[OH-].[Na+]>CO>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][S:13][CH3:14])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20362815N-{4-[(Methylsulfanyl)methoxy]-2-nitrophenyl}acetamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.7 G. of 1-acetamido-4-methylthiomethoxy-2-nitrobenzene is added to a mixture of 12 ml. 5N NaOH and 60 ml. methanol and the mixture heated for 15 minutes on a steam bath. The mixture is poured into 500 ml. water and is extracted with methylene chloride. The methylene chloride layer is separated, dried over sodium sulfate, and evaporated leaving 1-amino-4-methylthiomethoxy-2-nitrobenzene as a gum. This gum is dissolved in a mixture of 5 ml. acetic acid and 95 ml. methanol. 8 G. of iron powder is added and the mixture is heated at reflux for 2 hours. The methanol and acetic acid are evaporated and the residue is extracted with 200 ml. hot tetrahydrofuran. This solution is filtered and the tetrahydrofuran evaporated to yield 1,2-diamino-4-methylthiomethoxybenzene as a gum. This is purified by column chromatography.

Workup

  1. additionThe mixture is poured into 500 ml
  2. extractionwater and is extracted with methylene chloride
  3. customThe methylene chloride layer is separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ae6996ac1b0847d6a76ba7df27c356e0
Source dataset
uspto-grants-1977_01
Patent number
US04002640

Reaction notes

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