Acetamidine monohydrochloride → HCID 178467223, compound

HRID 1979807Notes

Reaction equation

HRID 1979807 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 75.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.66 g (10 mmole) 2-chloro-1,1-dimethoxy-3-butanone, 1.43 g (15 mmole) acetamidine hydrochloride and 2.05 g (25 mmole) sodium acetate in 50 ml dioxane is heated at reflux for 24 hours. The dioxane is evaporated in vacuo and the residual oil is flash chromatographed on silica gel (40:60 ethyl acetate/hexane, 40 mm) to obtain three fractions. The third fraction, a white solid (1.121 g) was rechromatographed (40 mm, acetone) to afford 933 mg (75.1%) of product as white solid which is pure as judged by its NMR spectrum in CDCl3 and by TLC on silica gel (one spot, 1:9 methanol/chloroform).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 24 hours
  3. customThe dioxane is evaporated in vacuo
  4. customchromatographed on silica gel (40:60 ethyl acetate/hexane, 40 mm)
  5. customto obtain three fractions
  6. customThe third fraction, a white solid (1.121 g) was rechromatographed (40 mm, acetone)

Sources & evidence

ORD record
ord-a3a1abfa6cbe4a99a8e3c91926f0eb40
Source dataset
uspto-grants-1984_11
Patent number
US04482723

Reaction notes

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