Pyridine → HCID 18981004, compound
Reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].Br[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:8].Cl[C:17]([O:19][CH3:20])=[O:18].N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([N:4]([CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:8])[C:17]([O:19][CH3:20])=[O:18])[C:2]#[CH:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
To 25 g (454 mmole) of propargylamine in 200 ml of methylene chloride cooled to -40° C. was rapidly added 46 g (200 mmole) of 2-bromo-4'-chloroacetophenone dissolved in 200 ml of methylene chloride. The temperature rose to 0° C. and was maintained there for 15 minutes. The reaction mixture was washed with 250 ml of 1M sodium hydroxide and recooled to -20° C. whereon 22 g (233 mmole) of methyl chloroformate was added while maintaining an internal temperature of -20° C., then 20 g (253 mmole) of pyridine was added. After stirring for 1 hour the mixture was concentrated in vacuo, partitioned between diethyl ether and water, washed with dilute hydrochloric acid, washed with brine, dried over anhydrous magnesium sulfate, reconcentrated in vacuo, and chromatographed over silica gel using diethyl ether and hexanes to yield 34 g of the expected compound, an oil.
Workup
- customrose to 0° C.
- temperaturewas maintained there for 15 minutes
- washThe reaction mixture was washed with 250 ml of 1M sodium hydroxide
- customrecooled to -20° C.
- additionwas added
- concentrationwas concentrated in vacuo
- custompartitioned between diethyl ether and water
- washwashed with dilute hydrochloric acid
- washwashed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customchromatographed over silica gel
Sources & evidence
- ORD record
- ord-7aba11c3e55f4e9ea9956b8483775b60
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05798311
Reaction notes
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