1-Bromopropane → Ethyl 2-acetylamino-2-cyanopentanoate

HRID 392661

Reaction equation

[Na].[C:2]([NH:5][CH:6]([C:12]#[N:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].Br[CH2:15][CH2:16][CH3:17]>C(O)C>[C:2]([NH:5][C:6]([C:12]#[N:13])([CH2:15][CH2:16][CH3:17])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

1.35 g of sodium (58.8 mmol) are dissolved in 200 ml of ethanol and the resulting solution is cooled down to 0° C. 10 g (58.8 mmol) of ethyl acetamidocyanoacetate are added. After a clear solution has formed, a solution of 7.23 g (58.8 mmol) of bromopropane in 10 ml of ethanol is added dropwise and the reaction mixture is stirred at room temperature for 2 hours. A solution of 7.23 g (58.8 mmol) of bromopropane in 10 ml of ethanol is added once again and the reaction mixture is heated under reflux for 16 hours. The solvent is removed in vacuo and the residue is taken up in dichloromethane; the solution is washed with water and dried over magnesium sulfate. The solvent is removed in vacuo and the residue is stirred up with petroleum ether. After filtering off with suction, 7.5 g (60%) of ethyl 2-acetylamino-2-cyanopentanoate are obtained.

Workup

customAfter a clear solution has formed
temperaturethe reaction mixture is heated
temperatureunder reflux for 16 hours
customThe solvent is removed in vacuo
washthe solution is washed with water
dry with materialdried over magnesium sulfate
customThe solvent is removed in vacuo
stirringthe residue is stirred up with petroleum ether
filtrationAfter filtering off with suction, 7.5 g (60%) of ethyl 2-acetylamino-2-cyanopentanoate
customare obtained

Sources & evidence

ORD record: ord-1ccc1a8d732748e58c16ad9bbbaa3e25
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06803365B2

Linked notes

Loading…