1,1'-Carbonyldiimidazole → 6-Trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 496270Notes

Reaction equation

HRID 496270 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[F:13][C:14]([F:24])([F:23])[C:15]1[CH:16]=[C:17]([NH2:22])[C:18]([NH2:21])=[N:19][CH:20]=1>C(Cl)Cl>[F:24][C:14]([F:13])([F:23])[C:15]1[CH:16]=[C:17]2[NH:22][C:1](=[O:2])[NH:21][C:18]2=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 102144255-(Trifluoromethyl)pyridine-2,3-diamine

Product 1

HCID 117153916-Trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 1,1′-carbonyldiimidazole (1.0 g, 6.17 mmol) to a solution of 5-trifluoromethyl-pyridine-2,3 diamine (0.90 g, 5.08 mmol) in CH2Cl2 (10 mL) and stir at room temperature for 18 hours. Heat the solution to reflux for 2 hours and filter the precipitate to obtain 6-trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one. C. 2-Chloro-6-trifluoromethyl-3-H-imidazo[4,5-b]pyridine

Workup

  1. temperatureHeat the solution
  2. temperatureto reflux for 2 hours
  3. filtrationfilter the precipitate

Sources & evidence

ORD record
ord-4798a267e12b40d5a09aca7bf6f86591
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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