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

HRID 616145Notes

Reaction equation

HRID 616145 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)C=O.[H-].[Na+].[CH2:19]([O:21][CH2:22]Cl)[CH3:20]>O>[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([S:11][CH2:22][O:21][CH2:19][CH3:20])=[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 dimethylformamide is treated with 0.5 g. of 100% sodium hydride. After 1 hour, 2.2 g. of chloromethyl ethyl ether is added. After a further hour, the solution is diluted with water and extracted with chloroform. Removal of the solvent leaves 2-nitro-5-(ethoxymethylthio)aniline.

Workup

  1. waitAfter a further hour
  2. extractionextracted with chloroform
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-2677004e60764aab959b24c1a350d6a3
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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