Nitric Acid → 4-Acetamido-3-nitrophenylsulphur pentafluoride

HRID 849662Notes

Reaction equation

HRID 849662 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N+:17]([O-])([OH:19])=[O:18].S(=O)(=O)(O)O>C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([F:12])([F:13])([F:16])([F:14])[F:15])=[CH:7][C:6]=1[N+:17]([O-:19])=[O:18])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 21576972N-[4-(Pentafluorosulfanyl)phenyl]acetamide

Product 1

HCID 545377794-Acetamido-3-nitrophenylsulphur pentafluoride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Acetamidophenylsulphur pentafluoride (27.0 g) was added during 5 minutes to a stirred mixture of concentrated nitric acid and concentrated sulphuric acid (1 part:2 parts by volume) at 0-5° C. After 5 minutes acetic acid (1 part) was added and stirring continued at 5° C. for 1.5 hours. The mixture was added to ice/water, extracted (ethyl acetate) and the extract washed (sodium carbonate solution), dried (magnesium sulphate) and evaporated. The residue was triturated with ether to give 4-acetamido-3-nitrophenylsulphur pentafluoride (30.0 g), m.p.135-138° C.

Workup

  1. extractionextracted (ethyl acetate)
  2. washthe extract washed (sodium carbonate solution)
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated
  5. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-0f3c21b04c0041c589555537589a533f
Source dataset
uspto-grants-2000_01
Patent number
US06013805

Reaction notes

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