Chlorosuccinimide → HCID 10219735, compound
Reaction equation
[CH2:1]([NH:7][C:8](=[O:11])[C:9]#[CH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CCCCCC.C([Li])CCC.[Cl:23]N1C(=O)CCC1=O>C1COCC1.O.C(OCC)(=O)C>[CH2:1]([NH:7][C:8](=[O:11])[C:9]#[C:10][Cl:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
Conditions
- Temperature
- -78 °C
Procedure
2.45 g of N-(n-hexyl)propiolamide was dissolved in 40 ml of dry THF, which was cooled to -78° C. 20 ml of n-butyllithium hexane solution (1.6 mol/1) was added thereto, and the mixture was stirred for 10 minutes. 4.28 g of N-chlorosuccinimide was added thereto, and the resultant mixture was stirred at -78° C. for 2 hours. The mixture was allowed to be warmed to -30° C., to which 10 ml of water was added. The mixture was then stirred overnight at a room temperature. Ethyl acetate and water were added to the reaction solution for separation. An organic phase was concentrated under reduced pressure. A residue was purified by the silica gel column chromatography (eluent: ethyl acetate/hexane=1/9). N-(n-hexyl)-3-chloropropiolamide (2.50 g) was obtained as a colorless oil.
Workup
- additionwas added
- stirringThe mixture was then stirred overnight at a room temperature
- concentrationAn organic phase was concentrated under reduced pressure
- customA residue was purified by the silica gel column chromatography (eluent: ethyl acetate/hexane=1/9)
Sources & evidence
- ORD record
- ord-137cb98602b04d3b9e0e55d63f3accec
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05538998
Reaction notes
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