2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → HCID 20438532, compound

HRID 1979702Notes

Reaction equation

HRID 1979702 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]#[N:18])[C:12](OCC)=O)C>C(O)C>[C:17]([C:11]1[C:10](=[O:9])[N:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[N:1][CH:12]=1)#[N:18]

Participants

4

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 18368243HCID 18368243, compound

Product 1

HCID 20438532HCID 20438532, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-5 °C

Procedure

16.8 g of 2-amino-pyrroline are dissolved in 140 ml of ethanol and the solution is cooled to -5° C. and under stirring added dropwise to a solution of 33.8 g of ethyl ethoxy-methylene-cyanoacetate in 250 ml of ethanol. The reaction mixture is allowed to warm up to room temperature, and boiled for one hour. The reaction is then allowed to crystallize under cooling below 0° C. The precipitated crystals are filtered and thus 13.7 g (42.5%) of 3-cyano-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine are obtained, melting at 119°-121° C. after recrystallization from ethanol.

Workup

  1. temperatureto warm up to room temperature
  2. customto crystallize
  3. temperatureunder cooling below 0° C
  4. filtrationThe precipitated crystals are filtered

Sources & evidence

ORD record
ord-a1e7314f7a7f431892ec705365213b51
Source dataset
uspto-grants-1984_11
Patent number
US04482557

Reaction notes

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