Thiophenol → 2-Nitro-5-phenylthioaniline
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1[CH:17]=[CH:16][C:15]([S-:18])=[CH:14][CH:13]=1.[Na+].[H-].[Na+].C1(S)C=CC=CC=1>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[C:6]([S:18][C:15]2[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]Participants
Reactant 4
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
- customprepared under nitrogen from 2.53 g
- washdimethylformamide rinse
- additiondiluted with water
- washThe crude product is washed with water and hexane
- customrecrystallized from methanol
Sources & evidence
- ORD record
- ord-f7b403893c274b0ea9a8f10e49af786f
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04002640
Reaction notes
Loading…