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

HRID 1163863Notes

Reaction equation

HRID 1163863 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 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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 an 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. additionadded dropwise to a solution of 33.8 g
  2. waitboiled for an hour
  3. customto crystallize
  4. temperatureunder cooling below 0° C
  5. filtrationThe precipitated crystals are filtered

Sources & evidence

ORD record
ord-399097d8f29946ee9ee75d4c1d6b30ce
Source dataset
uspto-grants-1983_01
Patent number
US04367229

Reaction notes

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