Acetamidine monohydrochloride → HCID 178467223, compound

HRID 1979806Notes

Reaction equation

HRID 1979806 reaction equation
Cl[CH:2]([C:8](=[O:10])[CH3:9])[CH:3](OC)OC.Cl.[C:12]([NH2:15])(=[NH:14])[CH3:13].C([O-])(=O)C.[Na+]>O1CCOCC1>[C:8]([C:2]1[N:14]=[C:12]([CH3:13])[NH:15][CH:3]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 517045Sodium AcetateHCID 155879453-Chloro-4,4-dimethoxybutan-2-one

Product 1

HCID 178467223HCID 178467223, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 500 ml of dioxane are added 83.5 g (0.50 mole) 2-chloro-1,1-dimethoxy-3-butanone, 94.5 g (1.0 mole) acetamidine hydrochloride and 123 g (1.5 mole) sodium acetate and the mixture is heated at reflux overnight. The cooled reaction mixture is filtered through a silica gel pad on a sintered glass filter funnel, washing with 3500 ml of dioxane. The filtrate and washings are combined and evaporated in vacuo to provide a residual oil which is purified by chromatography on a silica gel column (600 g), eluting with ethyl acetate. Fractions of 200 ml each are collected. After 16 fractions the elution is with 95:5 ethyl acetate/methanol. Fractions 18-35 are combined and the solvent evaporated in vacuo to afford 28.82 g (46.4%) of the desired product. Recrystallization from 1:1 ethyl acetate/isopropyl ether yields 19.27 g (31%) of crystals, M.P. 132°-133° C. Another 4.24 g (6.8%) was obtained by reworking the mother liquor. 1H-NMR (CD3OD) ppm (delta): 2.40 (s, 3H), 2.43 (s, 3H), 7.68 (s, 1H).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. customThe cooled reaction mixture
  4. filtrationis filtered through a silica gel pad on a sintered glass
  5. filtrationfilter funnel
  6. washwashing with 3500 ml of dioxane
  7. customevaporated in vacuo
  8. customto provide a residual oil which
  9. customis purified by chromatography on a silica gel column (600 g)
  10. washeluting with ethyl acetate
  11. customFractions of 200 ml each are collected
  12. washAfter 16 fractions the elution
  13. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-658aff55cdd74814b410a121fdc8a20d
Source dataset
uspto-grants-1984_11
Patent number
US04482723

Reaction notes

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