Benzenesulfonyl chloride, 4-chloro-3-nitro- → Benzenesulfonamide, 4-chloro-N-methyl-3-nitro-

HRID 536046

Reaktionsgleichung

Reaktionsgleichung von HRID 536046
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[CH3:16][NH2:17]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:17][CH3:16])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Komponenten

5

Edukt 2

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 6364545Methylamine hydrochloride

Produkt 1

HCID 67301Benzenesulfonamide, 4-chloro-N-methyl-3-nitro-Ausbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-3-nitrobenzenesulfonyl chloride (10 g, 39.1 mmol) in THF (100 mL) was cooled to −40° C. before being treated with a solution of methylamine hydrochloride (2.64 g, 39.1 mmol) in 10 ml of water followed by TEA (5.44 mL, 39.1 mmol). The reaction mixture was stirred and allowed to warm to room temperature over 1 hour before being partitioned between 350 mL EtOAc and 30 mL brine. The organic layer was washed twice with brine, dried over MgSO4 and subjected to flash chromatography (330 g silica gel, 0-40% EtOAc/hexane) to afford 4-chloro-N-methyl-3-nitrobenzenesulfonamide (6.38 g, 65%) as a light yellow solid. MS (m/z) 251.0 (M+H+).

Aufarbeitung

  1. custombefore being partitioned between 350 mL EtOAc and 30 mL brine
  2. washThe organic layer was washed twice with brine
  3. dry with materialdried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-0f87bf007f8d43d0813b84f4291b22b7
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859571B2

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