Ethyl bromoacetate → HCID 67391626, compound

HRID 910862Notes

Reaction equation

HRID 910862 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[Cl:19])[CH:3]=1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[Cl:19])[CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetate2×HCID 517045Sodium Acetate2×HCID 67390461HCID 67390461, compound

Product 1

HCID 67391626HCID 67391626, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the product from step (i) (0.3 g), ethyl bromoacetate (0.22 ml) and sodium acetate (0.164 g) in dry ethanol (5 ml) was heated under reflux 7 h. Ethyl bromoacetate (0.5 ml) and sodium acetate (0.34 g) were added and heated for a further 16 h. The solvent was evaporated under reduced pressure and the residue purified by chromatography on silica eluting with 5-7% ethylacetate/isohexane, yield 0.212 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux 7 h
  3. temperatureheated for a further 16 h
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue purified by chromatography on silica eluting with 5-7% ethylacetate/isohexane, yield 0.212 g

Sources & evidence

ORD record
ord-955d79b1fd924e8d976a8273f870b9ae
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

Loading…