Urea → 4,6-dichloro-1,3-dihydro-2H-Imidazo[4,5-c]pyridin-2-one
Reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([NH2:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.N[C:12](N)=[O:13]>O>[Cl:1][C:2]1[C:7]2[NH:8][C:12](=[O:13])[NH:9][C:6]=2[CH:5]=[C:4]([Cl:10])[N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 165 °C
Procedure
A mixture of 2,6-dichloro-3,4-dihydropyridine-3,4-diamine (500 mg, 2.8 mmol) from Step B and urea (1.0 g, 16.8 mmol) was stirred as a melt at 165° C. for 4 h, then cooled and H2O (100 mL) was added. The aqueous mixture was heated at reflux until all solid dissolved and the solution was allowed to cool and aged for 18 h. The precipitate was isolated by filtration to give the title compound. MS: m/z=204 (M+1).
Workup
- temperaturecooled
- temperatureThe aqueous mixture was heated
- temperatureat reflux until all solid
- dissolutiondissolved
- temperatureto cool
- waitaged for 18 h
- customThe precipitate was isolated by filtration
Sources & evidence
- ORD record
- ord-1ba83228612e460e922ef26fa60936f6
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08133891B2
Reaction notes
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