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

HRID 1258531Notes

Reaction equation

HRID 1258531 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>C(Cl)Cl>[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

4

Reactant 2

HCID 1118Sulfuric AcidHCID 58085708HCID 58085708, compound

Product 1

HCID 581368521-[3-Amino-5-(pentafluorosulfanyl)phenyl]ethanoneYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

N-(3-Acetyl-5-pentafluorosulfanylphenyl)-2,2,2-trifluoroacetamide (9.4 g, example 4d) was admixed with semiconcentrated sulfuric acid (200 ml), and DCM (15 ml) was added for dissolution. After stirring at 100° C. for 7 h, the mixture was left to stand overnight. Then the mixture was added to ice-water and extracted with EA. The combined EA phases were washed with saturated sodium hydrogencarbonate solution, dried over magnesium sulfate, filtered and concentrated by rotary evaporation. 6.36 g of the title compound were obtained.

Workup

  1. additionwas added for dissolution
  2. waitthe mixture was left
  3. waitto stand overnight
  4. extractionextracted with EA
  5. washThe combined EA phases were washed with saturated sodium hydrogencarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-5f8ead2868da49cbbf0e2e1ecaaaa304
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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