Ammonia → 5-methylpyrazine-2-carboxamide

HRID 1414858Notes

Reaction equation

HRID 1414858 reaction equation
[C:1]([C:4]1[CH:9]=[N:8][C:7]([CH3:10])=[CH:6][N:5]=1)(O)=[O:2].ClC(OCC)=O.[NH3:17]>O1CCOCC1.C(N(CCCC)CCCC)CCC>[C:1]([C:4]1[CH:9]=[N:8][C:7]([CH3:10])=[CH:6][N:5]=1)(=[O:2])[NH2:17]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 10928Ethyl chloroformateHCID 1228315-Methyl-2-pyrazinecarboxylic acid

Product 1

HCID 27600545-methylpyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 7622TributylamineSolventHCID 312751,4-DioxaneSolvent2×

Procedure

2-Carboxy-5-methylpyrazine (9.7 g) in dry dioxan (114 ml) and tributylamine (17.7 ml) was treated with ethyl chloroformate (7.5 ml), keeping the temperature at 0°-5° C. After ten minutes, dioxan (190 ml) saturated with ammonia was added. The mixture was stirred for 3 hours at room temperature, then dioxan was distilled off, and the residue was taken up in saturated aqueous sodium bicarbonate (20 ml). The mixture was filtered and the product washed with water to give 2-carbamoyl-5-methylpyrazine (9.2 g), m.p. 204°- 206° C. This amide (7 g) in glacial acetic acid (30 ml) and 35% hydrogen peroxide (20 ml.) was heated with stirring at 70° C for 7 hours. The reaction mixture was cooled, the product which separated was filtered and washed with water to give 2-carbamoyl-5-methylpyrazine 4-oxide (5.5 g), m.p. 206°- 208° C.

Workup

  1. customat 0°-5° C
  2. waitAfter ten minutes
  3. distillationdioxan was distilled off
  4. filtrationThe mixture was filtered
  5. washthe product washed with water

Sources & evidence

ORD record
ord-04c433d750ee4987b90d7c876aefa8cf
Source dataset
uspto-grants-1977_01
Patent number
US04002750

Reaction notes

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