Nitrogen → HCID 20367213, compound

HRID 460889Notes

Reaction equation

HRID 460889 reaction equation
[Na].C([O:4][C:5](=O)[CH2:6][C:7]#[N:8])C.[CH3:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[CH2:14][NH:15][NH2:16].N#N>C(O)C.O>[NH2:8][C:7]1[NH:16][N:15]([CH2:14][C:13]2[CH:17]=[CH:18][CH:19]=[C:11]([CH3:10])[CH:12]=2)[C:5](=[O:4])[CH:6]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 7764Ethyl cyanoacetateHCID 5360545SodiumHCID 16774220[(3-Methylphenyl)methyl]hydrazine

Product 1

HCID 20367213HCID 20367213, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4.6 g of sodium are dissolved in 100 ml of ethanol. A mixture of 12 g of cyanoacetic acid ethyl ester and 13.6 g of 3-methylbenzylhydrazine is added to this solution. The mixture is heated to the boil for 5 hours while stirring and passing N2 into it. After driving off the solvent, taking up the residue in water, extracting with ether and clarifying with animal charcoal, acidification with acetic acid yields colorless crystals which after again being recrystallised from ethanol melt at 92°. The yield is 10.3 g of the compound identified above, corresponding to 51% of theory.

Workup

  1. additionis added to this solution
  2. temperatureThe mixture is heated to the boil for 5 hours
  3. extractionextracting with ether
  4. customyields colorless crystals which
  5. customafter again being recrystallised from ethanol
  6. custommelt at 92°

Sources & evidence

ORD record
ord-ea43ecf1a272426ca350617196abbfe8
Source dataset
uspto-grants-1977_12
Patent number
US04061653

Reaction notes

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