Ethanol → HCID 178457168, compound

HRID 647138Notes

Reaction equation

HRID 647138 reaction equation
Cl.[O:2]1C=CC=C1C=CC(=N)OCC.C(O)C.N#CN.[CH:20]1([NH:26][C:27](=[N:37][C:38]#[N:39])[CH:28]=[CH:29][C:30]2C=C[CH:33]=[CH:32][C:31]=2Cl)CCC[CH2:22][CH2:21]1>C(OCC)(=O)C.C(N(CC)CC)C>[CH2:20]([NH:26][C:27](=[N:37][C:38]#[N:39])[CH:28]=[CH:29][C:30]1[O:2][CH:33]=[CH:32][CH:31]=1)[CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 702EthanolHCID 9864CyanamideHCID 70533875HCID 70533875, compoundHCID 178512135HCID 178512135, compound

Product 1

HCID 178457168HCID 178457168, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-(2-furyl)-2-propenimidate HCl in an amount of 1.34 g. is dissolved in 3 ml. of ethanol and then an equimolar amount of triethylamine is added to the ice-cooled resulting solution. To this solution, cyanamide (0.25 g.) is added and stirring is continued for 1 hour at room temperature. After removal of solvent from the mixture, the resulting residue is dissolved in ethyl acetate. The ethyl acetate layer is washed with water and dried with MgSO4. To the residue, after removal of ethyl acetate, MeOH (3 ml.) and n-butylamine (1.1 g.) are added with slight warming and stirring is continued for 1 hour. The mixture is evaporated and resulting residue is submitted to column chromatography (KIESEL GEL 40 T : ethyl acetate for eluent). The thus obtained crystals, which are recrystallized from acetone have the formula: ##STR11## and the following characteristics:

Workup

  1. dissolutionis dissolved in 3 ml
  2. temperaturecooled
  3. customresulting solution
  4. customAfter removal of solvent from the mixture
  5. dissolutionthe resulting residue is dissolved in ethyl acetate
  6. washThe ethyl acetate layer is washed with water
  7. dry with materialdried with MgSO4
  8. customTo the residue, after removal of ethyl acetate, MeOH (3 ml.) and n-butylamine (1.1 g.)
  9. additionare added
  10. temperaturewith slight warming
  11. stirringstirring
  12. waitis continued for 1 hour
  13. customThe mixture is evaporated
  14. customresulting residue
  15. customThe thus obtained crystals, which are recrystallized from acetone

Sources & evidence

ORD record
ord-d53c216ccc9b494aac278fc538222d1d
Source dataset
uspto-grants-1983_10
Patent number
US04407816

Reaction notes

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