Hydrochloric Acid → HCID 178441827, compound

HRID 1971038Notes

Reaction equation

HRID 1971038 reaction equation
[O-]CC.[Na+].C(O)(=O)C.[CH3:9][CH:10]([CH3:15])[CH2:11][C:12](=[NH:14])[NH2:13].Cl.C(O[C:20](=[NH:27])[CH2:21][C:22](OCC)=[O:23])C.Cl>C(O)C.O>[NH2:27][C:20]1[N:13]=[C:12]([CH2:11][CH:10]([CH3:15])[CH3:9])[N:14]=[C:22]([OH:23])[CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 2723922Sodium ethoxide2×HCID 44607755HCID 44607755, compound

Product 1

HCID 178441827HCID 178441827, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

Sodium ethoxide (210 mL of a 21% solution in ethanol, 563 mmol) was diluted with absolute ethanol (290 mL). To the sodium ethoxide solution were then sequentially added 3-methylbutanimidamide acetate (45 g, 281 mmol) and ethyl 3-ethoxy-3-iminopropionate hydrochloride (59 g 85% purity, 256 mmol) and the mixture was heated to reflux overnight. The mixture was cooled down, solvent was stripped off and the residue was diluted with water (100 mL). pH was adjusted to 6-7 with 2 N HCl and the slurry was heated to reflux. Water (350 mL) was added although total dissolution of the solids was not achieved. The solids were collected by filtration and dried under vacuum to yield 18.6 g of the title compound. Upon cooling additional product precipitated, that was isolated by filtration and dried under vacuum to yield additional 8.18 g of product. The combined solids accounted for a total of 26.8 g (yield: 62%).

Workup

  1. temperatureto reflux overnight
  2. temperatureThe mixture was cooled down
  3. temperaturethe slurry was heated to reflux
  4. filtrationThe solids were collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7fc878e74e6543779b14bf0889850748
Source dataset
uspto-grants-2013_04
Patent number
US08431580B2

Reaction notes

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