Pyridine → N-(2-ethyl-5-nitrophenyl)methanesulfonamide

HRID 889445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889445
[CH2:1]([C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5])[CH3:2].N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH2:1]([C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH:5][S:20]([CH3:19])(=[O:22])=[O:21])[CH3:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 41554782-Ethyl-5-nitroaniline

Produkt 1

HCID 59313849N-(2-ethyl-5-nitrophenyl)methanesulfonamideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-ethyl-5-nitroaniline (200 mg, 1.20 mmol) in DCM (5 mL) was added pyridine (0.195 mL, 2.41 mmol) and methanesulfonyl chloride (0.11 mL, 1.44 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with DCM, washed with water and brine and dried to give Intermediate 78A (290 mg, 99%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.35 (1H, d, J=2.26 Hz), 8.04 (1H, dd, J=8.53, 2.26 Hz), 7.44 (1H, d, J=8.53 Hz), 6.59 (1H, br. s.), 3.15 (3H, s), 2.76 (2H, q, J=7.53 Hz), 1.32 (3H, t, J=7.53 Hz).

Aufarbeitung

  1. washwashed with water and brine
  2. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9c0d50d0b5834ef385326a2714392f5a
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252795B2

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