Ethyl bromoacetate → HCID 22241166, compound

HRID 891970Notes

Reaction equation

HRID 891970 reaction equation
[CH2:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])[C:2]#[CH:3].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[O-2].[Mg+2]>CC(N(C)C)=O>[CH2:18]([O:17][C:15]([CH2:14][N:4]([CH2:1][C:2]#[CH:3])[C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 6850729Magnesium monoxideHCID 11286598HCID 11286598, compound

Product 1

HCID 22241166HCID 22241166, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 0.78 g (5 mmol) of 3-propargylamino-benzonitrile, 0.55 ml (5 mmol) of ethyl bromoacetate and 0.2 g (5 mmol) of magnesium oxide are stirred in 20 ml of dimethylacetamide for 6 days at 75° C. Then the mixture is filtered, the filtrate is diluted with ethyl acetate and washed with water. The combined organic extracts are dried and concentrated by evaporation. The residue is chromatographed on silica gel, eluting with dichloromethane.

Workup

  1. filtrationThen the mixture is filtered
  2. additionthe filtrate is diluted with ethyl acetate
  3. washwashed with water
  4. customThe combined organic extracts are dried
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-865c7ffd048e4e29911063c0d8277f0e
Source dataset
uspto-grants-2006_02
Patent number
US07005437B2

Reaction notes

Loading…