Dimethylformamide → 5-[(Ethoxymethyl)sulfanyl]-2-nitroaniline
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
Product 1
Reagents, catalysts & solvents 1
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
- waitAfter a further hour
- extractionextracted with chloroform
- 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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