Ethyl Acetate → N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamide

HRID 432966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432966
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([N+:14]([O-])=O)[CH:8]=1)(=[O:5])=[O:4].C(OCC)(=O)C>C(O)(=O)C.[Fe]>[NH2:14][C:9]1[CH:8]=[C:7]([NH:6][S:3]([CH2:2][Cl:1])(=[O:4])=[O:5])[CH:12]=[CH:11][C:10]=1[F:13]

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 18760842chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

Produkt 1

HCID 18760845N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 12.5 g of iron powder (223 mmol) and 16 mL of an aqueous solution of acetic acid (8%) was heated to 80° C., and a solution of 6 g of I -chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide (22.3 mmol) in 20 mL of glacial acetic acid and 22 mL ethyl acetate was added dropwise to the mixture. After heating for 1.5 h the reaction mixture was filtered through a pad of Celite® and washed with 200 mL of ethyl acetate and water (twice with 25 mL). The organic phase was separated, dried (MgSO4), filtered and concentrated under reduced pressure to yield 5 g (94%) of the title compound as a solid melting at 128-129° C.

Aufarbeitung

  1. temperatureAfter heating for 1.5 h the reaction mixture
  2. filtrationwas filtered through a pad of Celite®
  3. washwashed with 200 mL of ethyl acetate and water (twice with 25 mL)
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bef168359c1344ba9cf349bd425414a3
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664400B2

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