Acetic Anhydride → N-[2-Nitro-5-(phenylsulfanyl)phenyl]acetamide

HRID 596582Notes

Reaction equation

HRID 596582 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

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 1707372-Nitro-5-phenylthioanilineHCID 517045Sodium Acetate

Product 1

HCID 20362827N-[2-Nitro-5-(phenylsulfanyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

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-chloro-1-nitrobenzene with sodium phenylmercaptide essentially as described above for the free amine.

Workup

  1. customthe solvent removed under vacuum
  2. additionThe residue is treated with water
  3. filtrationfiltered
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-b42b2fba97f6424580eaa02c7ef887a4
Source dataset
uspto-grants-1977_03
Patent number
US04011320

Reaction notes

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