Ethanol → HCID 12535800, compound

HRID 437429Notes

Reaction equation

HRID 437429 reaction equation
[Na].C(O)C.Cl.[CH2:6]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[NH:12])[CH3:7].C([O:20][CH:21]=[C:22]([C:28](OCC)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])C>C(O)(=O)C>[O:20]=[C:21]1[NH:13][C:11]([C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[O:8][CH2:6][CH3:7])=[N:12][CH:28]=[C:22]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 6871Diethyl (ethoxymethylene)malonateHCID 5360545SodiumHCID 123012442-Ethoxybenzamidine hydrochloride

Product 1

HCID 12535800HCID 12535800, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a cooled solution of sodium (8.2 g., 0.356 g-atom) in 300 ml. ethanol was added all at once 2-ethoxybenzamidine hydrochloride (35.7 g., 0.178 mole). A solution of diethyl ethoxymethylenemalonate (38.4 g., 0.178 mole) in 80 ml. of ethanol was added to the suspension and the mixture was heated under reflux for 21/4 hours. The cooled solution was added to about 2800 ml. of ice-water and the mixture was acidified to pH 5 with glacial acetic acid. The precipitated title product was dried to give 47 g. of an off-white solid, m.p. 147°-150°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 21/4 hours
  3. additionThe cooled solution was added to about 2800 ml
  4. customThe precipitated title product
  5. customwas dried
  6. customto give 47 g

Sources & evidence

ORD record
ord-ec099405c0c5465ca9eb53d63f7fc8e7
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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