4-Aminopyridine → 1-(2,6-Dichlorophenyl)-3-(4-pyridyl)urea

HRID 368295Notes

Reaction equation

HRID 368295 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[N:16]=[C:17]=[O:18]>O1CCCC1>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[NH:16][C:17]([NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)=[O:18]

Participants

4

Reactant 2

HCID 17274-AminopyridineHCID 6045371,3-Dichloro-2-isocyanatobenzene

Product 1

HCID 46105601-(2,6-Dichlorophenyl)-3-(4-pyridyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.7 g (0.05 mol) of 4-aminopyridine in 300 mL of anhydrous tetrahydrofuran was treated with 9.4 g (0.05 mol) of 2,6-dichlorophenylisocyanate. The solution was heated at reflux for 24 hours, cooled, and concentrated in vacuo to a solid. Recrystallization from aqueous ethanol afforded the crystalline product, mp 217-219° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 24 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo to a solid
  5. customRecrystallization from aqueous ethanol
  6. customafforded the crystalline product, mp 217-219° C.

Sources & evidence

ORD record
ord-3bfc791bba3b426ebce9e41954e978a1
Source dataset
uspto-grants-2000_10
Patent number
US06133299

Reaction notes

Loading…