Dimethylformamide → 5-[(Ethoxymethyl)sulfanyl]-2-nitroaniline

HRID 1679462Notes

Reaction equation

HRID 1679462 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].CN(C=O)C.[H-].[Na+].Cl[CH2:20][O:21][CH2:22][CH3:23]>O>[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([S:11][CH2:20][O:21][CH2:22][CH3:23])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 213180223-Amino-4-nitrobenzene-1-thiol

Product 1

HCID 203712005-[(Ethoxymethyl)sulfanyl]-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.4 g. of 2-nitro-5-mercaptoaniline in 20 ml. of DMF is treated with 0.5 g. of 100% sodium hydride, and 2.2 g. of chloromethyl-ethyl ether is added to the solution. After 30 minutes at 20°-25° C, the solution is diluted with water and extracted with chloroform. Removal of the chloroform leaves 2-nitro-5-(ethoxymethylthio) aniline as an oil.

Workup

  1. extractionextracted with chloroform
  2. customRemoval of the chloroform

Sources & evidence

ORD record
ord-2e0016253a8f401ca60545fc40d98184
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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