HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 392661
Notes
Print preview

Reaction equation

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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 78401-Bromopropane2×HCID 95422Ethyl acetamidocyanoacetateHCID 5360545Sodium

Product 1

HCID 11593708Ethyl 2-acetylamino-2-cyanopentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

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

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

Sources & evidence

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

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes