Diethyl (ethoxymethylene)malonate → HCID 12778919, compound

HRID 1163870Notes

Reaction equation

HRID 1163870 reaction equation
[NH2:1][C:2]1[NH:3][CH2:4][CH2:5][CH:6]=1.C([O:9][CH:10]=[C:11]([C:17](OCC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])C>C(O)C>[O:9]=[C:10]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][N:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[N:1]1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 18368243HCID 18368243, compound

Product 1

HCID 12778919HCID 12778919, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

42 g. of 2-amino-pyrroline are dissolved in 400 ml. of ethanol and at 0°-7° C. a solution of 108 g. of diethyl ethoxy-methylene-malonate in 200 ml. ethanol is added dropwise. After the addition is completed the mixture is stirred for 1 hour at 0° C., and allowed to stand for 12 hours at -5° C. The precipitated crystals are filtered. After evaporation of the alcohol the residue is boiled with 200 ml. of benzene. After cooling the insoluble crystals are filtered off. The filtered crystals are combined and recrystallized from ethanol. 50.3 g. (48.4%) ethyl 2-oxo-2,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-3-carboxylate are obtained, melting at 193° C.

Workup

  1. customat 0°-7° C.
  2. additionAfter the addition
  3. waitto stand for 12 hours at -5° C
  4. filtrationThe precipitated crystals are filtered
  5. customAfter evaporation of the alcohol the residue
  6. temperatureAfter cooling the insoluble crystals
  7. filtrationare filtered off
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-da0cdb2cbb93440eb458eff6b5fe0f29
Source dataset
uspto-grants-1983_01
Patent number
US04367229

Reaction notes

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