Methanesulfonyl chloride → Methanesulfonamide, N-[2-iodo-4-(trifluoromethyl)phenyl]-

HRID 1171463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171463
[I:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH2:12].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[I:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][S:14]([CH3:13])(=[O:16])=[O:15]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 27833222-Iodo-4-(trifluoromethyl)aniline

Produkt 1

HCID 21075164Methanesulfonamide, N-[2-iodo-4-(trifluoromethyl)phenyl]-Ausbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 2-iodo-4-(trifluoromethyl)benzenamine (11.0 g, 0.0382 mol), pyridine (40 ml), methanesulfonylchloride (5.3 g, 0.046 mol) and DMAP (0.46 g, 0.0038 mol) in a 100 ml RB flask was heated slowly to 105° C. and maintained the same temperature for over night. The reaction mixture was concentrated to remove the pyridine. The crude product obtained was purified by column chromatography using 10% ethyl acetate in pet ether as eluent to get N-(2-iodo-4-(trifluoromethyl)phenyl)methanesulfonamide (4.5 g, 32%) as white solid. 1H NMR (400 MHz, CDCl3) δ 3.08 (s, 3H), 6.88 (bs, 1H), 7.65 (d, 1H), 7.75 (d, 1H), 8.07 (s, 1H).

Aufarbeitung

  1. temperaturemaintained the same temperature for over night
  2. concentrationThe reaction mixture was concentrated
  3. customto remove the pyridine
  4. customThe crude product obtained
  5. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c136f2dc6bfb4c35bc68c185cd013f30
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829571B2

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