Ethanesulfonylchloride, 2-chloro- → HCID 86702164, Verbindung

HRID 1776244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776244
[CH3:1][C:2](=[CH2:5])[CH2:3][NH2:4].C(N(CC)C(C)C)(C)C.Cl[CH2:16][CH2:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:5][C:2](=[CH2:1])[CH2:3][NH:4][S:18]([CH:17]=[CH2:16])(=[O:20])=[O:19]

Komponenten

5

Edukt 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 761412-MethylallylamineHCID 81531Diisopropylethylamine

Produkt 1

HCID 86702164HCID 86702164, VerbindungAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-methylprop-2-en-1-amine (0.500 g, 7.0 mmol), N,N-diisopropylethylamine (3.486 mL, 21.1 mmol) and N,N-4-dimethylaminopyridine (0.043 g, 0.4 mmol) in methylene chloride (20 mL) at 0° C. was slowly added 2-chloroethanesulfonyl chloride (0.734 mL, 7.0 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 16 hrs. The mixture was concentrated and the residue purified by silica gel chromatography (0-80% ethyl acetate/hexanes) to afford the product as a colorless oil (0.59 g, 52%). 1H NMR (300 MHz, CDCl3) δ 6.54 (dd, 1H, J=16.5, 9.6 Hz), 6.27 (d, 1H, J=16.5 Hz), 5.96 (d, 1H, J=9.6 Hz), 4.97 (s, 1H), 4.93 (s, 1H), 4.37 (br s, 1H), 3.60 (d, 2H, J=6.3 Hz), 1.79 (s, 3H).

Aufarbeitung

  1. customat 0° C.
  2. concentrationThe mixture was concentrated
  3. customthe residue purified by silica gel chromatography (0-80% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-739c5e71f62249ffaba44eeb895119c4
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265772B2

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