HCID 20488278, compound → HCID 13066355, compound

HRID 1995317Notes

Reaction equation

HRID 1995317 reaction equation
[NH2:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([CH3:9])=[N:3]1.C([O:12][CH:13]=[C:14]([C:18]#[N:19])[C:15]([O-])=O)C>C(O)C>[C:18]([C:14]1[C:13](=[O:12])[N:3]2[CH:4]([CH3:9])[CH2:5][CH2:6][CH2:7][CH2:8][C:2]2=[N:1][CH:15]=1)#[N:19]

Participants

4

Reactant 2

HCID 20488278HCID 20488278, compoundHCID 53400745HCID 53400745, compound

Product 1

HCID 13066355HCID 13066355, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-5 °C

Procedure

2.52 g. of 2-amino-7-methyl-3,4,5,6-tetrahydro-2H-azepine are dissolved in 25 ml. of ethanol and the solution is added dropwise to a solution of 3.38 g. of ethoxy-methylene-cyanoacetate in 25 ml. ethanol at -5° C. The reaction mixture is stirred for 1 hour at -5° C. and allowed to warm up to room temperature and boiled for 1 hour. The solvent is evaporated. The residual oil is dissolved in 40 ml. of benzene and the solution is shaken out once with 10 ml. of 5% by W/V sodium carbonate solution and twice with 10 ml. of water. The benzene layer is dried above sodium sulphate and evaporated after filtration. The residual oil is crystallized from acetone. 1.26 g. (31%) 3-cyano-6-methyl-4-oxo-4,6,7,8,9,10-hexahydro-pyrimido[1,2-a]azepine is obtained melting at 154° C.

Workup

  1. customat -5° C
  2. temperatureto warm up to room temperature
  3. waitboiled for 1 hour
  4. customThe solvent is evaporated
  5. dissolutionThe residual oil is dissolved in 40 ml
  6. stirringof benzene and the solution is shaken out once with 10 ml
  7. dry with materialThe benzene layer is dried above sodium sulphate
  8. customevaporated
  9. filtrationafter filtration
  10. customThe residual oil is crystallized from acetone

Sources & evidence

ORD record
ord-f525dfee74b5434db703b145d58637db
Source dataset
uspto-grants-1983_09
Patent number
US04404205

Reaction notes

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