Hydrochloric Acid → HCID 12535800, compound

HRID 437428Notes

Reaction equation

HRID 437428 reaction equation
[Na].[CH2:2]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=[NH:8])[CH3:3].C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])C.Cl>C(O)C>[O:16]=[C:17]1[NH:9][C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][CH2:2][CH3:3])=[N:8][CH:24]=[C:18]1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 32510232-ethoxybenzamidineHCID 5360545Sodium

Product 1

HCID 12535800HCID 12535800, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a cooled solution of sodium (1.04 g., 0.045 g-atom) in 35 ml. of ethanol was added all at once 2-ethoxybenzamidine (7.4 g., 45 mmole). There was then added to this suspension over a 5 minute period a solution of diethyl ethoxymethylenemalonate (9.7 g., 45 mmole) in 20 ml. of ethanol whereupon a pale yellow precipitate soon formed. An additional 25 ml. of ethanol was added to the reaction mixture which was then heated under reflux for 21/4 hours. The cooled solution was poured into about 500 ml. of ice-water and acidified with 6N HCl to produce a pale yellow solid. The solid was dried to give 10.2 g., m.p. 144°-149°, of title product. Recrystallization from acetonitrile gave 9.8 g., m.p. 147°-150°, of purified product.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 21/4 hours
  3. additionThe cooled solution was poured into about 500 ml
  4. customto produce a pale yellow solid
  5. customThe solid was dried
  6. customto give 10.2 g

Sources & evidence

ORD record
ord-ed6b5c13fcb24fa386617356a267761b
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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