Di(succinimido) carbonate → 1-Allyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one
Reaction equation
C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:3](=[O:4])C1.[CH2:19]([NH:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([Cl:29])[C:24]=1[NH2:30])[CH:20]=[CH2:21]>C(#N)C>[CH2:19]([N:22]1[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([Cl:29])[C:24]=2[NH:30][C:3]1=[O:4])[CH:20]=[CH2:21]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 400 ml acetonitrile solution of 4.46 g of N,N′-disuccinimidyl carbonate was added to an acetonitrile solution containing 2.88 g of N*4*-allyl-2-chloropyridine-3,4-diamine, and the mixture was heated under reflux for 70 hours. The solvent was concentrated under reduced pressure, and the residue was dissolved in a mixture consisting of 500 ml of ethyl acetate and 300 ml of water. The organic layer was washed twice with 100 ml of 1N hydrochloric acid and then with 100 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 2.30 g of the title compound was obtained from the fraction eluted with ethyl acetate-dichloromethane (1:1).
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 70 hours
- concentrationThe solvent was concentrated under reduced pressure
- dissolutionthe residue was dissolved in a mixture
- washThe organic layer was washed twice with 100 ml of 1N hydrochloric acid
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-ab22a837b2de4c8c8df292c89553da9e
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772226B2
Reaction notes
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