1,1'-Carbonyldiimidazole → HCID 14390447, compound

HRID 1709603Notes

Reaction equation

HRID 1709603 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]([OH:21])=[O:20])[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:24]1C=CN=C1)=O>O1CCCC1>[OH2:20].[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]([NH2:24])=[O:21])[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 14390445HCID 14390445, compound

Product 1

HCID 14390447HCID 14390447, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5-chloro-2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.1 g, 0.00963 mole) and 1,1'-carbonyldiimidazole (1.56 g, 0.00963 mole) in tetrahydrofuran (100 ml) was refluxed under nitrogen for 1.5 hours, cooled to room temperature, and a stream of nitrogen was bubbled through the solution for one hour. The solution was cooled in a dry ice/acetone bath and liquid ammonia (50 ml) was added. The reaction mixture was allowed to warm to room temperature and was stirred at room temperature for two days. The solvents were removed under reduced pressure and the solid was triturated in water (100 ml), collected by filtration, and rinsed twice with water, twice with a 5% potassium hydroxide solution, and twice again with water. The solid was recrystallized twice from isopropyl alcohol/water and dried under high vacuum at 70° C. to give 1.78 g (54%) of title compound, mp >250° C.

Workup

  1. temperaturewas refluxed under nitrogen for 1.5 hours
  2. customa stream of nitrogen was bubbled through the solution for one hour
  3. temperatureThe solution was cooled in a dry ice/acetone bath
  4. additionliquid ammonia (50 ml) was added
  5. temperatureto warm to room temperature
  6. customThe solvents were removed under reduced pressure
  7. customthe solid was triturated in water (100 ml)
  8. filtrationcollected by filtration
  9. washrinsed twice with water, twice with a 5% potassium hydroxide solution
  10. customThe solid was recrystallized twice from isopropyl alcohol/water
  11. customdried under high vacuum at 70° C.

Sources & evidence

ORD record
ord-51e26db795bc46ae824f7fdd4c4f5a55
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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