Methanesulfonyl chloride → 3-Acetamido-6-chloro-2-fluorobenzyl methanesulfonate

HRID 1257163

Reaktionsgleichung

Reaktionsgleichung von HRID 1257163
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[C:3]=1[CH2:13][OH:14].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:15][S:16]([O:14][CH2:13][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[C:4]=1[F:12])(=[O:18])=[O:17]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 86713625N-(4-chloro-2-fluoro-3-(hydroxymethyl)phenyl)acetamide

Produkt 1

HCID 867136263-Acetamido-6-chloro-2-fluorobenzyl methanesulfonateAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 0° C. of N-(4-chloro-2-fluoro-3-(hydroxymethyl)phenyl)acetamide (1.05 g, 4.82 mmol) and TEA (1.003 mL, 7.24 mmol) in DCM (30 mL) was treated slowly with methanesulfonyl chloride (0.414 mL, 5.31 mmol), warmed to RT and stirred for 2 h. The mixture was treated with satd. NaHCO3, extracted with DCM (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 3-acetamido-6-chloro-2-fluorobenzyl methanesulfonate (1.31 g, 74% yield) as an off-white solid. MS (ESI) m/z: 296.0 [M+H]+.

Aufarbeitung

  1. additionThe mixture was treated with satd
  2. extractionNaHCO3, extracted with DCM (2×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b6cd181252794d948d2e9d900a4deed8
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461179B1

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