Acetic Acid → HCID 178493933, compound

HRID 729751

Reaction equation

HRID 729751 reaction equation
Cl.[CH:2]([NH2:4])=[NH:3].CC[O-].[Na+].[CH3:9][O:10][CH:11]([C:16](OC)=[O:17])[C:12](OC)=[O:13].C(O)(=O)C>C(O)C>[CH3:9][O:10][C:11]1[C:12]([OH:13])=[N:3][CH:2]=[N:4][C:16]=1[OH:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 78718Dimethyl methoxymalonateHCID 2723922Sodium ethoxideHCID 10313058Methanimidamide, hydrochloride (1:1)

Product 1

HCID 178493933HCID 178493933, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5 g (6.2 mmoles) of formamidine hydrochloride is added at 0° C. and in small quantities into a single-necked flask containing 30 ml of absolute ethanol and 90 ml of a solution of sodium ethylate at a concentration of 1.7 mol/l in ethanol. Stirring is maintained at ambient temperature for about twenty minutes, then 8.5 ml of dimethyl methoxymalonate is added dropwise. Stirring is maintained for 16 hours. The reaction mixture is then acidified with pure acetic acid to a pH between 4 and 5, then concentrated to dryness in the presence of cyclohexane. After impasting the crude product obtained is chromatographed on silicagel eluting with a mixture of methylene chloride-methanol (85-15)and 2% water-acetic acid (1-1). 9.5 g of the expected product is obtained containing a small quantity of sodium acetate salts.

Workup

  1. stirringStirring
  2. temperatureis maintained for 16 hours
  3. concentrationconcentrated to dryness in the presence of cyclohexane
  4. customobtained
  5. customis chromatographed
  6. washon silicagel eluting with a mixture of methylene chloride-methanol (85-15)and 2% water-acetic acid (1-1)

Sources & evidence

ORD record
ord-c196fe37c24c46fa8843bc802cc48135
Source dataset
uspto-grants-2009_09
Patent number
US07582640B2

Linked notes

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