Phosgene → HCID 9878953, compound
Reaction equation
ClC(Cl)=O.[Cl:5][C:6]1[CH:7]=[C:8](O)[CH:9]=[C:10]([Cl:12])[CH:11]=1.[C:14](=[O:17])([O-])[O-].[Cs+].[Cs+].O.[NH2:21][NH2:22]>CC(C)=O>[Cl:5][C:6]1[CH:7]=[C:8]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[O:17][C:14]1[C:8]([CH2:9][CH3:10])=[N:21][NH:22][C:11]=1[CH2:6][CH3:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of the chloroketone of Preparation 2 (5 g, 30.8 mmol), 3,5-dichlorophenol (5 g, 30.8 mmol), caesium carbonate (10 g, 30.8 mmol) and acetone (40 ml) was heated under reflux for 18 hours. After cooling, a solid was removed by filtration and washed with dichloromethane (100 ml). The combined filtrates were concentrated under reduced pressure. The crude product was dissolved in ethanol (20 ml), hydrazine hydrate (1.5 ml, 30.8 mmol) was added and the mixture was heated at 60° C. for 30 minutes under nitrogen. After cooling, the mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with ether:pentane (1:1, by volume) to provide the title compound (5.5 g) as a yellow oil which solidified on standing to leave a yellow solid, m.p. 114-115° C.
Workup
- temperaturewas heated
- temperatureunder reflux for 18 hours
- temperatureAfter cooling
- customa solid was removed by filtration
- washwashed with dichloromethane (100 ml)
- concentrationThe combined filtrates were concentrated under reduced pressure
- dissolutionThe crude product was dissolved in ethanol (20 ml)
- temperatureAfter cooling
- concentrationthe mixture was concentrated under reduced pressure
- customthe residue was purified by flash chromatography on silica gel eluting with ether:pentane (1:1, by volume)
Sources & evidence
- ORD record
- ord-32595199cfdd44378c7116ad0938f66e
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435728B2
Reaction notes
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