3-Aminopyridine → (E)-N-cinnamyl-N'-(3-pyridyl) urea

HRID 477003Notes

Reaction equation

HRID 477003 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].N[C:14]1C=NC=C[CH:19]=1.C(N)/C=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH2:12]([NH:8][C:1]([NH:3][C:7]1[CH:6]=[N:5][CH:4]=[CH:14][CH:19]=1)=[O:2])/[CH:11]=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 100093-AminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 6008559cinnamylamine

Product 1

HCID 14834216(E)-N-cinnamyl-N'-(3-pyridyl) ureaYield 233.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 50 ml of a tetrahydrofuran solution containing 16.2 g of carbonyldiimidazole, a solution of 9.4 g of 3-aminopyridine dissolved in 50 ml of tetrahydrofuran was added dropwise under ice-cooling over 5 minutes. After stirring under ice-cooling for 30 minutes and at room temperature for 1 hour, the mixture was again ice-cooled, and 1.33 g of (E)-cinnamylamine was added, followed by stirring at room temperature for 18 hours. After distilling the solvent off, the residue was dissolved in ethyl acetate, washed with water and dried, followed by distillation of the solvent. The residue was purified by silica gel column chromatography (solvent: chloroform-methanol=20:1) to give 5.9 g of (E)-N-cinnamyl-N'-(3-pyridyl) urea as colorless caramel.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling over 5 minutes
  3. temperaturecooled
  4. stirringby stirring at room temperature for 18 hours
  5. distillationAfter distilling the solvent off, the residue
  6. dissolutionwas dissolved in ethyl acetate
  7. washwashed with water
  8. customdried
  9. distillationfollowed by distillation of the solvent
  10. customThe residue was purified by silica gel column chromatography (solvent: chloroform-methanol=20:1)

Sources & evidence

ORD record
ord-97c44f7008054c8591a1d3f809c41caa
Source dataset
uspto-grants-1989_12
Patent number
US04886817

Reaction notes

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