Triethylamine → HCID 44574294, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[Cl:17][CH:18]([CH3:22])[C:19](Cl)=[O:20]>ClCCl>[Cl:17][CH:18]([CH3:22])[C:19]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1)=[O:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of 2-amino-5-cyanopyridine (0.500 g, 4.2 mmol) in dry dichloromethane (20 mL) was added triethylamine (0.830 g, 6.3 mmol) and the mixture was stirred at 0° C. To the reaction mixture, 2-chloropropionyl chloride (0.800 g, 6.3 mmol) was added dropwise, and the reaction mixture was stirred at 0° C. for an hour and then at room temperature for 48 hours. The reaction mixture was diluted with dichloromethane (100 mL) and was washed with water (150 mL). The reaction mixture was dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by column chromatography (silica gel, 15-20% ethyl acetate in petroleum ether as an eluent) to obtain the title compound.
Workup
- stirringthe reaction mixture was stirred at 0° C. for an hour
- washwas washed with water (150 mL)
- dry with materialThe reaction mixture was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customto obtain the crude product, which
- customwas purified by column chromatography (silica gel, 15-20% ethyl acetate in petroleum ether as an eluent)
Sources & evidence
- ORD record
- ord-2cc7b6b7adcc41ceaa2c0a1f37fa61f1
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314103B2
Reaction notes
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