3-Chloro-4-morpholinoaniline → 2-Butyl-4-[(3-chloro-4-morpholin-4-ylphenyl)amino]-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729291

Reaktionsgleichung

Reaktionsgleichung von HRID 729291
[CH2:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4].[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=1[N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)[NH2:24]>CC#N>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:24][C:23]2[CH:25]=[CH:26][C:27]([N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)=[C:21]([Cl:20])[CH:22]=2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 1086613-Chloro-4-morpholinoanilineHCID 672426232-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Produkt 1

HCID 117198592-Butyl-4-[(3-chloro-4-morpholin-4-ylphenyl)amino]-5-phenylisothiazol-3(2H)-one 1,1-dioxideAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 2-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.025 g, 0.083 mmol) and 3-chloro-4-morpholinoaniline (0.039 g, 0.183 mmol) in MeCN (1 ml) was heated in a microwave reactor at 130° C. for 90 mins. The product was purified by preparative HPLC (Kromasil C8, 0.1M NH4OAc/MeCN, gradient). The combined product fractions were evaporated and freeze-dried to give the title compound (0.004 mg, 9%). 1H NMR (400 MHz, CD3CN): δ 7.74 (bs, 1H), 7.29-7.24 (m, 1H), 7.20-7.15 (m, 2H), 7.12-7.08 (m, 2H), 6.80-6.75 (m, 3H), 3.76-3.71 (m, 6H), 2.85-2.81 (m, 4H), 1.85-1.76 (m, 2H), 1.52-1.42 (m, 2H), 1.00 (t, 3H); Mass Spectrum: M+H+ 476.

Aufarbeitung

  1. customThe product was purified by preparative HPLC (Kromasil C8, 0.1M NH4OAc/MeCN, gradient)
  2. customThe combined product fractions were evaporated
  3. customfreeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-951f80639f3f4bdc941c46291d947b7d
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582629B2

Verknüpfte Notizen

Wird geladen…