HCID 86747151, compound → HCID 178459029, compound

HRID 2255149Notes

Reaction equation

HRID 2255149 reaction equation
[CH2:1]([O:4][CH2:5][CH:6]([NH:9][C:10](=[O:18])[C:11](=[N:16][OH:17])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:7]#[N:8])[CH:2]=[CH2:3]>C(O)(=O)C>[CH2:1]([O:4][CH2:5][C:6]1[NH:9][C:10](=[O:18])[C:11]([CH2:12][CH:13]([CH3:14])[CH3:15])=[N+:16]([O-:17])[C:7]=1[NH2:8])[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 86747151HCID 86747151, compound

Product 1

HCID 178459029HCID 178459029, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To 220 ml of acetic acid was added 22 g of 3-allyloxy-2-(α-hydroxyiminoisocaproylamino)propionitrile. The mixture was subjected to a reaction for 1 hour at 85° C. After completion of the reaction, acetic acid was removed by evaporation under reduced pressure. The residue was purified by using Frorisil (60-100 mesh) (eluting solvent: 30 volume % ethyl acetate-n-hexane→ 60% volume of ethyl acetate-n-hexane), then washed with diethyl ether, followed by recrystallization from benzene, to obtain 5 g of 6-allyloxymethyl-5-amino-3-isobutyl-1,2-dihydropyrazin-2-one 4-oxide (Compound B-3) as pale yellow plate-like crystals having a melting point of 149°-151° C.

Workup

  1. customThe mixture was subjected to a reaction for 1 hour at 85° C
  2. customwas removed by evaporation under reduced pressure
  3. customThe residue was purified
  4. washFrorisil (60-100 mesh) (eluting solvent: 30 volume % ethyl acetate-n-hexane→ 60% volume of ethyl acetate-n-hexane)
  5. washwashed with diethyl ether
  6. customfollowed by recrystallization from benzene

Sources & evidence

ORD record
ord-d7857b521eca458ea61b2c71179cfaeb
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

Loading…