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

HRID 616098Notes

Reaction equation

HRID 616098 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

3.0 G. 2-amino-4-phenylthio-1-nitrobenzene (prepared according to Example XII) is dissolved in 40 ml. of acetic anhydride and two drops of sulfuric acid added. The mixture is left at room temperature for two hours then neutralized with a little sodium acetate and concentrated under vacuum. Water is added to the residue and the crude product filtered off. Recrystallization from methanol gives pure 2-acetamido-4-phenylthio-1-nitrobenzene.

Workup

  1. concentrationconcentrated under vacuum
  2. additionWater is added to the residue
  3. filtrationthe crude product filtered off
  4. customRecrystallization from methanol

Sources & evidence

ORD record
ord-e63217dab307430e91eec06fcc063b11
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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