Isocyanatocyclopropane → HCID 178521714, compound

HRID 1391222Notes

Reaction equation

HRID 1391222 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[N:3]=[CH:2]1.[CH:10]1([N:13]=[C:14]=[O:15])[CH2:12][CH2:11]1>O1CCOCC1.C(#N)C>[CH:10]1([NH:13][C:14]([N:6]2[CH2:7][CH2:8][C:9]3[NH:1][CH:2]=[N:3][C:4]=3[CH2:5]2)=[O:15])[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 637659IsocyanatocyclopropaneHCID 178420865HCID 178420865, compound

Product 1

HCID 178521714HCID 178521714, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3.69 g of 4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine and 7.47 g of cyclopropyl isocyanate in 20 ml of dry dioxane is refluxed for 1.5 h. After evaporation to dryness, the residue is dissolved in 44 ml of methanol and treated with 11 ml of 2N sodium hydroxide for 1.5 h at room temperature. After neutralization, the solution is extracted with chloroform. Evaporation of the solvent leaves a residue that is taken up in acetonitrile to give 2.12 g of the title compound, m.p. 215°.

Workup

  1. customAfter evaporation to dryness
  2. dissolutionthe residue is dissolved in 44 ml of methanol
  3. additiontreated with 11 ml of 2N sodium hydroxide for 1.5 h at room temperature
  4. extractionAfter neutralization, the solution is extracted with chloroform
  5. customEvaporation of the solvent
  6. customleaves a residue that

Sources & evidence

ORD record
ord-55cb4b3b45a04812abbc632eca4a0c4b
Source dataset
uspto-grants-1979_02
Patent number
US04141899

Reaction notes

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