Hydrochloric Acid → HCID 178430942, compound

HRID 2059741Notes

Reaction equation

HRID 2059741 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[N:5][N:6]([C:8](=[NH:10])[NH2:9])[CH:7]=1.C[O-].[Na+].C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21]CC)=[O:20])C.[OH-].[K+].Cl>CCO.CCOCC>[OH:16][C:17]1[C:18]([C:19]([OH:21])=[O:20])=[CH:24][N:9]=[C:8]([N:6]2[CH:7]=[C:3]([CH3:2])[CH:4]=[N:5]2)[N:10]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 14797Potassium Hydroxide2×HCID 10942334Sodium MethoxideHCID 45264782HCID 45264782, compound

Product 1

HCID 178430942HCID 178430942, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
78 °C

Procedure

The product of step A (9 g, 46.8 mmol), NaOMe (16.0 mL, 70.2 mmol, 25% wt in MeOH) and diethyl ethoxymethylenemalonate (9.55 mL, 46.8 mmol) was dissolved in EtOH (100 mL). The reaction was heated for 1 h at 78° C. and became very thick. The mixture was slightly cooled and KOH (5.25 g, 94 mmol, 4.5 M in water) was added and the reaction became a cake. EtOH (20 mL) was added and the reaction was reheated at 78° C. for 90 min. Additional KOH (0.88 g, 15.7 mmol, 1 M in water) and EtOH (15 mL) were added and the reaction was heated 1 h. The mixture was cooled and HCl (20.9 mL, 265 mmol, 12 N) was added slowly and the slurry was diluted with Et2O. The solids were filtered, suspended in HCl (0.6 M) and re-filtered. The product was washed with Et2O:EtOH (1:1) and then hexane affording the titled compound. HPLC/MS: 221.1 (M+1); Rt=1.41 min.

Workup

  1. temperatureThe mixture was slightly cooled
  2. temperaturethe reaction was heated 1 h
  3. temperatureThe mixture was cooled
  4. filtrationThe solids were filtered
  5. filtrationre-filtered
  6. washThe product was washed with Et2O:EtOH (1:1)

Sources & evidence

ORD record
ord-6c305ebea63d45c9b8122f696d1af901
Source dataset
uspto-grants-2012_10
Patent number
US08278304B2

Reaction notes

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