1-Chloroethyl chloroformate → N-Methyl-2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanamine

HRID 424534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424534
ClC(OC(Cl)C)=O.[CH3:8][N:9](C)[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][S:15][C:14]2[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:13]1=2>ClCCCl>[CH3:8][NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][S:15][C:14]2[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:13]1=2

Komponenten

4

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 59144138N,N-Dimethyl-2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanamine

Produkt 1

HCID 59144162N-Methyl-2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

1-Chloroethyl chloroformate (0.612 mL, 5.61 mmol) was added to a solution of N,N-dimethyl-2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanamine (1.0 g, 3.74 mmol) in 1,2-dichloroethane (20 mL) at 0° C. in an argon atmosphere. The solution was brought to room temperature and refluxed under vigorous stirring for 3 hours. The solution was concentrated and then refluxed in MeOH (20 mL). The solution was concentrated to give dark brown viscous oil (1.05 g, quantitative). 1H NMR (CDCl3) δ 7.96 (d, J=2.4 Hz, 1H), 7.86 (dd, J=2.7, 9.3 Hz, 1H), 6.67 (d, J=9.3 Hz, 1H), 3.85-3.82 (m, 2H), 3.55 (t, J=6.9 Hz, 2H), 3.03-3.00 (m, 2H), 2.86 (t, J=6.9 Hz, 2H), 2.48 (s, 3H); ESI-MS (m/z, %): 256, 254 (MH+, 100).

Aufarbeitung

  1. customwas brought to room temperature
  2. temperaturerefluxed
  3. concentrationThe solution was concentrated
  4. temperaturerefluxed in MeOH (20 mL)
  5. concentrationThe solution was concentrated
  6. customto give dark brown viscous oil (1.05 g, quantitative)

Quellen und Nachweise

ORD-Eintrag
ord-7791ed4bc1074953a561bff8b2208dd8
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106043B2

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