Methanol → HCID 178433460, compound

HRID 1615951Notes

Reaction equation

HRID 1615951 reaction equation
CO.Cl.[C:4]([NH2:7])(=[NH:6])[CH3:5].[CH3:8][CH:9]([C:15](OCC)=[O:16])[C:10](OCC)=[O:11].O>C(O)(=O)C>[CH3:5][C:4]1[N:7]=[C:10]([OH:11])[C:9]([CH3:8])=[C:15]([OH:16])[N:6]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 11857Diethyl methylmalonateHCID 67170Acetamidine monohydrochloride

Product 1

HCID 178433460HCID 178433460, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A single-necked flask containing 40 ml of methanol, placed under a nitrogen atmosphere, is cooled down to 0° C. using an ice bath, 9.72 g of sodium methylate (i.e. a solution concentration c=3 mol.l−1) is added to the reaction mixture then 5 g (53 mmoles) of acetamidine hydrochloride is added at 0° C. and in small quantities. Stirring is maintained at ambient temperature for about twenty minutes, then 8.3 ml of diethyl methylmalonate is added dropwise. Stirring is maintained for 3 hours. Then the methanol is condensed under reduced pressure (2 kPa). The crude product obtained is taken up with a minimum quantity of water, cooled down to 0° C. then acidified with pure acetic acid to a pH between 4 and 5. The white precipitate formed is filtered, rinsed with water, ethyl ether and pentane. Then the white product is dried over P2O5 under reduced pressure (0.2 kPa). 3.3 g of expected product is obtained.

Workup

  1. concentration9.72 g of sodium methylate (i.e. a solution concentration c=3 mol.l−1)
  2. additionis added to the reaction mixture
  3. temperatureis maintained at ambient temperature for about twenty minutes
  4. stirringStirring
  5. temperatureis maintained for 3 hours
  6. customcondensed under reduced pressure (2 kPa)
  7. customThe crude product obtained
  8. temperaturecooled down to 0° C.
  9. customThe white precipitate formed
  10. filtrationis filtered
  11. washrinsed with water, ethyl ether and pentane
  12. dry with materialThen the white product is dried over P2O5 under reduced pressure (0.2 kPa)

Sources & evidence

ORD record
ord-690d82ee6d1941cfa7da83679546f7f9
Source dataset
uspto-grants-2014_07
Patent number
US08765766B2

Reaction notes

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