Hydrogen Peroxide → 5-Bromopyrazine-2-carboxamide

HRID 1798237Notes

Reaction equation

HRID 1798237 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.C(=O)([O-])[O-:11].[K+].[K+].OO.O>CS(C)=O.CC(C)=O>[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([NH2:9])=[O:11])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 378187222-Bromo-5-cyanopyrazine

Product 1

HCID 582925675-Bromopyrazine-2-carboxamideYield 27.5%

Reagents, catalysts & solvents 1

HCID 21922538Acetone dimethyl sulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 5-bromo-pyrazine-2-carbonitrile (1.84 g, 10.0 mmol) and potassium carbonate (1.38 g, 10.0 mmol) in DMSO/acetone (16 mL, 1:3) was treated with H2O2 (2.42 mL, 25.0 mmol) at 65° C. over 15 min. The reaction was kept stirring at 65° C. 1 h. Water (2 mL) was added at 40° C. and the suspension was cooled to 0° C. The precipitate was filtered to give the title compound as a yellow solid (556 mg). 1H NMR (300 MHz, DMSO-d6) δ 9.06 (s, 1H), 8.94 (s, 1H), 8.34 (s, 1H), 7.92 (s, 1H).

Workup

  1. custom1 h
  2. temperaturethe suspension was cooled to 0° C
  3. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-635e9ca714c541c7abf8d297d4fcdbcb
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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