Potassium Hydroxide → 4-[2-(Ethylthio)ethoxy]-2-nitroaniline
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH-].[K+].[CH2:14]([S:16][CH2:17][CH2:18]Br)[CH3:15]>C(O)C>[CH2:14]([S:16][CH2:17][CH2:18][O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)[CH3:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-amino-3-nitrophenol (17.5 g.) in ethanol (300 ml.) was treated with solid potassium hydroxide (6.38 g.). The mixture was treated with a solution of 2 -bromoethyl ethyl thioether (21.2 g.) in ethanol (100 ml.), and stirred at room temperature for 4 hours. The reaction mixture was then concentrated in vacuo and the residue was dissolved in chloroform (200 ml.). The chloroform solution was washed with aqueous sodium bicarbonate solution (10% w/v; 200 ml.), dried over magnesium sulphate and evaporated to give 4-[2-(ethylthio)ethoxy]-2-nitroaniline (23.4 g.) in the form of a dark red oil, which was used in the next stage without further purification being necessary.
Workup
- concentrationThe reaction mixture was then concentrated in vacuo
- dissolutionthe residue was dissolved in chloroform (200 ml.)
- washThe chloroform solution was washed with aqueous sodium bicarbonate solution (10% w/v; 200 ml.)
- dry with materialdried over magnesium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-42fdb24aaa2b4af6bb014cb57e76fcd1
- Source dataset
- uspto-grants-1977_07
- Patent number
- US04034107
Reaction notes
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