Acetic Acid → HCID 19378763, compound

HRID 2210477Notes

Reaction equation

HRID 2210477 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:11][C:10](=[O:12])[C:9]([CH2:13][CH:14]([CH3:16])[CH3:15])=[N+:8]([O-:17])[C:7]=1[OH:18])=[O:5])[CH3:2].[CH2:19](OCC)C.[N+](=C)=[N-].C(O)(=O)C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[NH:11][C:10](=[O:12])[C:9]([CH2:13][CH:14]([CH3:15])[CH3:16])=[N+:8]([O-:17])[C:7]=1[O:18][CH3:19])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 178470404HCID 178470404, compound

Product 1

HCID 19378763HCID 19378763, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 5.45 g of 6-ethoxycarbonyl-5-hydroxy-3-isobutyl-1,2-dihydropyrazin-2-one 4-oxide in chloroform was added dropwise gradually about equivalent quantity of diethyl ether solution of diazomethane at -15° C. 30 Minutes after the addition, 0.5 ml of acetic acid was added to the reaction mixture, and this mixture was allowed to stand for 30 minutes. Then the whole mixture was washed with water, and the solvent was removed by distillation, to the thus obtained residue was added 30 ml of chloroform and dissolved by heating, then 200 ml of diisopropyl ether was added gradually thereto so as to form crystals. The precipitated crystals were collected by filtration, and said operation were repeated twice to obtain 3.10 g of 6-ethoxycarbonyl-3-isobutyl-5-methoxy-l,2-dihydropyrazin-2-one 4-oxide.

Workup

  1. additionwas added to the reaction mixture
  2. washThen the whole mixture was washed with water
  3. customthe solvent was removed by distillation, to the thus obtained residue
  4. additionwas added 30 ml of chloroform
  5. dissolutiondissolved
  6. temperatureby heating
  7. addition200 ml of diisopropyl ether was added gradually
  8. customso as to form crystals
  9. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-70187683046f4342979590f5dcce9012
Source dataset
uspto-grants-1995_10
Patent number
US05459142

Reaction notes

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