Dichloromethane → HCID 69921167, compound
Reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][CH:4]=1)#[N:2].[CH3:14][NH:15][CH2:16][CH2:17]N.[Cl:19]CCl>Cl.O1CCOCC1.C(O)C>[ClH:19].[CH3:14][N:15]1[CH2:16][CH2:17][N:2]=[C:1]1[C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:12][CH:13]=1Participants
Procedure
1.8 g (10.3 mmol) of ethyl 4-cyanobenzoate was dissolved in a mixture of 20 ml of 4 N solution of hydrogen chloride in dioxane and 5 ml of ethanol, and the obtained solution was stirred at room temperature for 3 days. The solvent was evaporated, and the residue was washed with ethyl acetate. The obtained crude product was dissolved in 20 ml of ethanol. 1.52 g (20.6 mmol) of N-methylethylenediamine was added to the obtained solution, and they were heated under reflux for 6 hours. The solvent was evaporated, and the obtained crude product was treated with dichloromethane as the extraction solvent in an ordinary manner. The obtained crude product was dissolved in 10 ml of concentrated hydrochloric acid, and the obtained solution was stirred at 50° C. overnight. The solvent was evaporated to obtain the crude title compound.
Workup
- customThe solvent was evaporated
- washthe residue was washed with ethyl acetate
- customThe obtained crude product
- temperaturewere heated
- temperatureunder reflux for 6 hours
- customThe solvent was evaporated
- customthe obtained crude product
- customThe obtained crude product
- stirringthe obtained solution was stirred at 50° C. overnight
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-49d684722a25418db4846cc4f49b48af
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06812231B2
Reaction notes
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