Methanesulfonamide → 5-Chloro-2-fluoro-4-methyl-N-(methylsulfonyl)benzamide

HRID 512047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512047
[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH3:13][S:14]([NH2:17])(=[O:16])=[O:15].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:17][S:14]([CH3:13])(=[O:16])=[O:15])=[O:8]

Komponenten

6

Edukt 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 580424465-Chloro-2-fluoro-4-methylbenzoic acid

Produkt 1

HCID 580423685-Chloro-2-fluoro-4-methyl-N-(methylsulfonyl)benzamideAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-chloro-2-fluoro-4-methylbenzoic acid (Preparation 21, 200 g, 1.06 mol) in DCM (1.4 L) were added methanesulphonamide (152 g, 1.6 mol), 4-(dimethylamino)pyridine (183 g 1.6 mol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (306 g, 1.6 mol). An exotherm of 30° C. was observed in the first 30 minutes, then the mixture was stirred at room temperature for 18 hours under a nitrogen atmosphere. The reaction mixture was washed with aqueous hydrochloric acid (4 M, 0.8 L). The organic layer was separated, washed with water (500 mL) and dried over sodium sulfate to yield a tan solid, which was recrystallised from hot EtOAc (0.9 L) by addition of n-heptane (100 mL) and cooling to afford the title compound (118 g, 45%).

Aufarbeitung

  1. customAn exotherm of 30° C.
  2. customwas observed in the first 30 minutes
  3. washThe reaction mixture was washed with aqueous hydrochloric acid (4 M, 0.8 L)
  4. customThe organic layer was separated
  5. washwashed with water (500 mL)
  6. dry with materialdried over sodium sulfate
  7. customto yield a tan solid, which
  8. customwas recrystallised from hot EtOAc (0.9 L) by addition of n-heptane (100 mL)
  9. temperaturecooling

Quellen und Nachweise

ORD-Eintrag
ord-1966949c10b645d8b589eedfdcda0f2a
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102621B2

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