Urea → 4,6-dichloro-1,3-dihydro-2H-Imidazo[4,5-c]pyridin-2-one

HRID 1696397Notes

Reaction equation

HRID 1696397 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]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 109319872,6-Dichloropyridine-3,4-diamine

Product 1

HCID 114697654,6-dichloro-1,3-dihydro-2H-Imidazo[4,5-c]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. temperaturecooled
  2. temperatureThe aqueous mixture was heated
  3. temperatureat reflux until all solid
  4. dissolutiondissolved
  5. temperatureto cool
  6. waitaged for 18 h
  7. customThe precipitate was isolated by filtration

Sources & evidence

ORD record
ord-83d716ad29d44afa876046a4a129947c
Source dataset
uspto-grants-2012_04
Patent number
US08163752B2

Reaction notes

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