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

HRID 1658576Notes

Reaction equation

HRID 1658576 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-ceef30e6d01e4eaba2da4294193ce685
Source dataset
uspto-grants-1976_06
Patent number
US03965113

Reaction notes

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