Diethyl (ethoxymethylene)malonate → HCID 12535798, compound

HRID 2082738Notes

Reaction equation

HRID 2082738 reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C(=O)([O-])[O-].[K+].[K+].Cl.[N+:23]([C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28]([NH2:30])=[NH:29])([O-:25])=[O:24]>C(O)C>[O:13]=[C:11]1[NH:30][C:28]([C:27]2[CH:31]=[CH:32][CH:33]=[CH:34][C:26]=2[N+:23]([O-:25])=[O:24])=[N:29][CH:4]=[C:5]1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 21271815BENZENECARBOXIMIDAMIDE,2-NITRO-,HYDROCHLORIDE

Product 1

HCID 12535798HCID 12535798, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl ethoxymethylenemalonate (0.73 g., 3.44 mmoles), potassium carbonate (0.95 g., 6.88 mmoles), and ethanol (11 ml.) were added to 2-nitrobenzamidine hydrochloride (0.69 g., 3.44 mmoles)(prepared according to general method disclosed in U.S. Pat. No. 2,450,386). The mixture was heated under reflux for 3.5 hours. The cooled mixture was filtered. The filtrate was poured into ice-water (150 ml.) and the pH adjusted to 6.0 with acetic acid. The precipitate was collected and dried to give the title compound (0.20 g., 20.2%), m.p. 171°-175°. Recrystallization from acetonitrile gave analytical material, m.p. 175°-177°.

Workup

  1. customprepared
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3.5 hours
  4. filtrationThe cooled mixture was filtered
  5. additionThe filtrate was poured into ice-water (150 ml.)
  6. customThe precipitate was collected
  7. customdried

Sources & evidence

ORD record
ord-7e1f9cc5bb334a0fb31d66b0865b39bd
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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