Dimethylformamide → HCID 178470316, compound

HRID 2255153Notes

Reaction equation

HRID 2255153 reaction equation
[NH2:1][C:2]1[N+:3]([O-:18])=[C:4]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:5](=[O:13])[NH:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(=O)([O-])O.[K+].CN(C)C=O.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][C:5]([O:13][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:4]([CH2:14][CH:15]([CH3:17])[CH3:16])[N+:3]=1[O-:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 516893Potassium BicarbonateHCID 178470403HCID 178470403, compound

Product 1

HCID 178470316HCID 178470316, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

There were mixed 1.00 g of 5-amino-6-ethoxycarbonyl-3-isobutyl-1,2-dihydropyrazin-2-one 4-oxide, 1.18 g of potassium hydrogencarbonate (powder), 20 ml of dry dimethylformamide and 932 μl of benzyl bromide. The mixture was stirred for 16 hours at room temperature to effect a reaction. After completion of the reaction, the reaction mixture was poured into 50 ml of ethyl acetate. The resulting mixture was washed with 30 ml of water three times. The aqueous layer was extracted with 30 ml of ethyl acetate twice. The extract was combined with the above ethyl acetate layer. The combined solution was washed with 30 ml of water twice, and dried over magnesium sulfate. The solvent was removed by evaporation. The residue was recrystallized from ethanol to obtain 1.06 g of 2-amino-5-benzyloxy-3-ethoxycarbonyl-6-isobutylpyrazine 1-oxide (Compound B-10) as pale yellow fine needle-like crystals having a melting point of 114.5°-115.5° C.

Workup

  1. customa reaction
  2. customAfter completion of the reaction
  3. washThe resulting mixture was washed with 30 ml of water three times
  4. extractionThe aqueous layer was extracted with 30 ml of ethyl acetate twice
  5. washThe combined solution was washed with 30 ml of water twice
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed by evaporation
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-ec9d5954941c4148a20930837f903ea4
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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