Ethanol → 3-Trifluoromethyl-imidazo[1,2-B][1,2,4]triazine

HRID 891858Notes

Reaction equation

HRID 891858 reaction equation
C(OC(O[CH2:8][CH3:9])CBr)C.C(O)C.C(=O)([O-])O.[Na+].[NH2:18][C:19]1[N:20]=[N:21][CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[N:24]=1>Br.O>[F:27][C:25]([F:26])([F:28])[C:23]1[CH:22]=[N:21][N:20]2[CH:8]=[CH:9][N:18]=[C:19]2[N:24]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 516892Sodium BicarbonateHCID 115428325-(Trifluoromethyl)-1,2,4-triazin-3-amine

Product 1

HCID 116224693-Trifluoromethyl-imidazo[1,2-B][1,2,4]triazineYield 22.5%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of bromoacetaldehyde diethyl acetal (2.30 ml, 14.8 mmol) in concentrated hydrobromic acid (0.73 ml) and water (0.73 ml) was heated at reflux for 2 h, then poured into ethanol (25 ml). The solution was neutralised to pH 7 with solid sodium hydrogencarbonate, then filtered. To the filtrate was added 3-amino-5-trifluoromethyl-1,2,4-triazine (1.0079 g, 6.14 mmol) and the mixture was stirred at 60° C. for 20 h, then 80° C. for 23 h. The mixture was evaporated in vacuo, and the residue was purified by flash chromatography (silica gel, 35-50% EtOAc/isohexane) to give 0.2593 g (22%) of the title compound: 1H NMR (360 MHz, CDCl3) δ 8.20 (1H, d, J0.8), 8.30 (1H, d, J 0.9), 8.73 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationfiltered
  4. wait80° C. for 23 h
  5. customThe mixture was evaporated in vacuo
  6. customthe residue was purified by flash chromatography (silica gel, 35-50% EtOAc/isohexane)

Sources & evidence

ORD record
ord-bd11bcd6ae594eafb2d8970b7f820a1d
Source dataset
uspto-grants-2006_02
Patent number
US07005431B2

Reaction notes

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