Sodium methanethiolate → (4-Bromo-phenyl)-[4-(5-chloro-2-methyl-phenyl)-6-methylsulfanyl-[1,3,5]triazin-2-yl]-amine

HRID 1435741

Reaktionsgleichung

Reaktionsgleichung von HRID 1435741
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13](Cl)[N:12]=[C:11]([C:16]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=3[CH3:23])[N:10]=2)=[CH:4][CH:3]=1.[CH3:24][S-:25].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]=[C:11]([C:16]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=3[CH3:23])[N:12]=[C:13]([S:25][CH3:24])[N:14]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 4378561Sodium methanethiolateHCID 10179730(4-Bromo-phenyl)-[4-chloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-YL]-amine

Produkt 1

HCID 10112949(4-Bromo-phenyl)-[4-(5-chloro-2-methyl-phenyl)-6-methylsulfanyl-[1,3,5]triazin-2-yl]-amineAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of the title compound of Example 20 (234 mg, 0.57 mmol), sodium thiomethoxide (50 mg, 0.71 mmol), and tetrahydrofuran (5 ml) was stirred for 24 hours. After concentrating under reduced pressure, the residue was dissolved in dichloromethane (25 ml). The solution was washed with water (25 ml) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (1:1) to provide the title compound (137 mg, 57% yield). 1H NMR (DMSO-d6) 10.42 (s, 1H), 7.88 (s, 1H), 7.70 (s, 2H), 7.45-7.55 (m, 3H), 7.38 (m, 1H), 2.55 (s, 3H), 2.50 (s, 3H).

Aufarbeitung

  1. concentrationAfter concentrating under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (25 ml)
  3. washThe solution was washed with water (25 ml)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-19055edf0b534c87881dd5fa256cadfe
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618968B2

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