Hydrochloric Acid → HCID 178469940, compound

HRID 589166Notes

Reaction equation

HRID 589166 reaction equation
CC[O-].[Na+].C([O:7][CH:8]=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10](OCC)=O)C.O.[NH2:21][NH2:22].Cl>CCO>[OH:7][C:8]1[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][NH:22][N:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 24654Hydrazine hydrate (1:1)HCID 2723922Sodium ethoxide

Product 1

HCID 178469940HCID 178469940, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of NaOEt in EtOH (60 mL, 21 w %) were added diethyl 2-(ethoxymethylene)malonate (10.4 mL, 52.0 mmol) and hydrazine monohydrate (5.04 mL, 104 mmol) with cooling in an ice-water bath. The resulting mixture was then heated at 80° C. for 4 h. After cooling to rt, HCl (1 N, 180 mL) was added to the reaction mixture and then extracted with EtOAc three time. The combined organic layers were washed with brine and dried over Na2SO4. A solid obtained after evaporation was washed with ether and dried under high vacuum to afford the titled compound as an off-white solid (4.42 g), which was used without further purification.

Workup

  1. temperaturewith cooling in an ice-water bath
  2. temperatureAfter cooling to rt
  3. extractionextracted with EtOAc three time
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customA solid obtained
  7. customafter evaporation
  8. washwas washed with ether
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-1802e7cb80b843dbbd878452f2130e1d
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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