Hydrogen Bromide → HCID 11564642, Verbindung

HRID 895108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895108
CO[CH:3](OC)[CH2:4]Br.Br.C(=O)([O-])O.[Na+].[NH2:14][C:15]1[C:16](=[O:24])[N:17]([CH3:23])[C:18]([S:21][CH3:22])=[N:19][N:20]=1>CC(O)C.CO.O>[CH3:23][N:17]1[C:16](=[O:24])[C:15]2=[N:14][CH:3]=[CH:4][N:20]2[N:19]=[C:18]1[S:21][CH3:22]

Komponenten

8

Edukt 4

HCID 260Hydrogen BromideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 516892Sodium BicarbonateHCID 115428516-Amino-4-methyl-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one

Produkt 1

HCID 11564642HCID 11564642, VerbindungAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Bromoacetaldehyde dimethyl acetal (2.57 g, 13.1 mmol), 48% hydrobromic acid (1.06 g, 13.1 mmol) and water (1.5 ml) were heated at 95° C. for 1.5 h. The mixture was allowed to cool to ambient temperature, diluted with propan-2-ol (20 ml) then treated with sodium hydrogen-carbonate (1.46 g, 17.4 mmol) added in portions over 5 min. The mixture was filtered and the filtrate was added to 6-amino-4-methyl-3-methylsulfanyl-4H-[1,2,4]triazin-5-one (1.50 g, 8.71 mmol). The resulting suspension was heated at 95° C. for 18 h. The mixture was allowed to cool to ambient temperature, diluted with methanol (100 ml) and evaporated onto silica. The product was purified by flash column chromatography on silica eluting with dichloromethane (+0.1% 0.880 ammonia) on a gradient of methanol (3-6%). Collecting appropriate fractions gave 3-methyl-2-methylsulfanyl-3H-imidazo[2,1-f][1,2,4]triazin-4-one (0.81 g, 47%) as a pale yellow solid: δH (400 MHz, CDCl3) 2.61 (3H, s), 3.58 (3H, s), 7.49 (1H, d, J1), 7.52 (1H, d, J1).

Aufarbeitung

  1. additionadded in portions over 5 min
  2. filtrationThe mixture was filtered
  3. temperatureThe resulting suspension was heated at 95° C. for 18 h
  4. temperatureto cool to ambient temperature
  5. customevaporated onto silica
  6. customThe product was purified by flash column chromatography on silica eluting with dichloromethane (+0.1% 0.880 ammonia) on a gradient of methanol (3-6%)
  7. customCollecting appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-e08e8b942b9947eebdad846b05b4f39a
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06914060B2

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