Hydrochloric Acid → HCID 12535802, compound

HRID 437433Notes

Reaction equation

HRID 437433 reaction equation
Cl.[CH:2]([O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH2:10])=[NH:9])([CH3:4])[CH3:3].[Na].C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C.Cl>C(O)C.C(O)(=O)C>[O:18]=[C:19]1[NH:10][C:8]([C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH:2]([CH3:4])[CH3:3])=[N:9][CH:26]=[C:20]1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 5360545SodiumHCID 2036027163874-28-2

Product 1

HCID 12535802HCID 12535802, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

2-Isopropoxybenzamidine hydrochloride (10.0 g., 0.0465 mole) was added to a stirred, cooled (ice-water) solution of sodium 2.14 g., 0.093 g-atom) in ethanol (100 ml.). To this cooled, stirred solution was added dropwise a solution of diethyl ethoxymethylenemalonate (10.1 g., 0.0465 mole) in ethanol (30 ml.) over a 10 minute period. The mixture was refluxed for 2 hours and stored at 22° for 18 hours. The mixture was then poured onto ice-water containing acetic acid (10 ml.) and concentrated HCl (10 ml.) to precipitate the desired product. The precipitate was washed and dried to give 15.5 g. of the title product, m.p. 123° 124°. Recrystallizations from ethyl acetate and then cyclohexane gave colorless crystals of the ester, m.p. 128°-130°.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. additionThe mixture was then poured onto ice-water
  3. customto precipitate the desired product
  4. washThe precipitate was washed
  5. customdried
  6. customto give 15.5 g

Sources & evidence

ORD record
ord-a6787fa31eb449368a2312559c04bc77
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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