Sulfuric Acid → 1-[3-Amino-5-(pentafluorosulfanyl)phenyl]ethanone

HRID 1258519Notes

Reaction equation

HRID 1258519 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:16]C(=O)C(F)(F)F)[CH:7]=[C:8]([S:10]([F:15])([F:14])([F:13])([F:12])[F:11])[CH:9]=1)(=[O:3])[CH3:2].S(=O)(=O)(O)O>O.C(#N)C>[NH2:16][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[C:8]([S:10]([F:15])([F:11])([F:12])([F:13])[F:14])[CH:7]=1

Participants

5

Reactant 2

HCID 1118Sulfuric Acid2×HCID 58085708HCID 58085708, compound

Product 1

HCID 581368521-[3-Amino-5-(pentafluorosulfanyl)phenyl]ethanoneYield 86.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

N-(3-Acetyl-5-pentafluorosulfanylphenyl)-2,2,2-trifluoroacetamide (4 g, for preparation see example 4d) was suspended in 6 ml of water and 12 ml of acetonitrile, and 6 ml of concentrated sulfuric acid were added dropwise to this suspension. After stirring at 75° C. for 4 h and leaving to stand at RT overnight, the reaction was completed by adding another 2 ml of concentrated sulfuric acid and heating the mixture at 75° C. for 3 h. The reaction mixture was poured onto ice-water and extracted with ethyl acetate. The ethyl acetate phase was washed to neutrality with saturated sodium hydrogencarbonate solution, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by means of chromatography on silica gel. The product-containing fractions were combined and the solvent (heptane/ethyl acetate) was concentrated under reduced pressure. 2.53 g of 1-[3-amino-5-(pentafluorosulfanyl)phenyl]ethanone were obtained.

Workup

  1. customleaving
  2. waitto stand at RT overnight
  3. temperatureheating the mixture at 75° C. for 3 h
  4. additionThe reaction mixture was poured onto ice-water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate phase was washed to neutrality with saturated sodium hydrogencarbonate solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by means of chromatography on silica gel
  11. concentrationthe solvent (heptane/ethyl acetate) was concentrated under reduced pressure

Sources & evidence

ORD record
ord-598badac10e94cdc968260e0e07a30b1
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

Loading…