Acetic Anhydride → N-[2-Nitro-5-(phenylsulfanyl)phenyl]acetamide
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[C:18](OC(=O)C)(=[O:20])[CH3:19].C([O-])(=O)C.[Na+]>S(=O)(=O)(O)O>[C:18]([NH:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16])(=[O:20])[CH3:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
5 G. of 2-amino-4-chloro-1-nitrobenzene is added to a solution of sodium phenyl mercaptide, prepared under nitrogen from 2.53 g. 57% sodium hydride and 6.2 ml. thiophenol in 20 ml. dimethylformamide, with a 10 ml. dimethylformamide rinse. The mixture is stirred under nitrogen for three hours at 20°-30° C and then diluted with water. The crude product is washed with water and hexane, then recrystallized from methanol, yielding 2-amino-4-phenylthio-1-nitrobenzene. 6.0 G. of 2-amino-4-phenylthio-1-nitrobenzene is dissolved in 80 ml. acetic anhydride and treated with a few drops of sulfuric acid. The mixture is left at 20°-30° C for 2 hours then a little sodium acetate added and the solvent removed under vacuum. The residue is treated with water, filtered and recrystallized from methanol yielding 2-acetamido-4-phenylthio-1-nitrobenzene. This material may also be obtained by reaction of 2-acetamido-4-chloro1-nitrobenzene with sodium phenylmercaptide essentially as described above for the free amine.
Workup
- customthe solvent removed under vacuum
- additionThe residue is treated with water
- filtrationfiltered
- customrecrystallized from methanol
Sources & evidence
- ORD record
- ord-79a0ad17019b4666bbc2da19215e1789
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04002640
Reaction notes
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