Acetic Anhydride → N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]acetamide

HRID 1258506Notes

Reaction equation

HRID 1258506 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[NH2:8][C:9]1[CH:10]=[C:11]([C:21](=[O:23])[CH3:22])[CH:12]=[C:13]([S:15]([F:20])([F:19])([F:18])([F:17])[F:16])[CH:14]=1.C(N(CC)CC)C.C(OC(=O)C)(=O)C>C(Cl)Cl>[C:21]([C:11]1[CH:10]=[C:9]([NH:8][C:3](=[O:5])[CH3:2])[CH:14]=[C:13]([S:15]([F:16])([F:20])([F:17])([F:18])[F:19])[CH:12]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic Anhydride2×HCID 8471TriethylamineHCID 86650835HCID 86650835, compound

Product 1

HCID 58136897N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]acetamideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[3-Amino-5-(pentafluorosulfanyl)phenyl]ethanone trifluoroacetic acid salt (100 mg, example 4d) was dissolved in methylene chloride (10 ml), and triethylamine (120 μl) was added. Acetic anhydride (30 μl) was then added dropwise while stirring. After stirring for 4 h, the mixture was left to stand overnight and then further acetic anhydride (30 μl) was added. After stirring for a further 6 h, the reaction mixture was again left to stand overnight and then concentrated. The residue was taken up with ethyl acetate and water, and adjusted to pH 9 with saturated sodium hydrogencarbonate solution, and the aqueous phase was extracted twice more with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 80 mg of the desired compound were obtained.

Workup

  1. stirringAfter stirring for 4 h
  2. waitthe mixture was left
  3. stirringAfter stirring for a further 6 h
  4. waitthe reaction mixture was again left
  5. waitto stand overnight
  6. concentrationconcentrated
  7. extractionthe aqueous phase was extracted twice more with ethyl acetate
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-84a17dc9ada34f0abb0cc44e92e3d9b7
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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