Ethyl Bromide → HCID 21426790, compound

HRID 437727Notes

Reaction equation

HRID 437727 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].[CH2:8]([Mg]Br)[CH3:9].C(Br)C.[Mg].[Cl-].[NH4+]>C(OCC)C>[NH:2]=[C:1]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 5

HCID 6332Ethyl BromideHCID 7747Methyl cyanoacetateHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 178418443HCID 178418443, compound

Product 1

HCID 21426790HCID 21426790, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl cyanoacetate (99 g.) was added to a stirred solution of ethyl magnesium bromide [prepared by the method well known in the art, from ethyl bromide (328 g.) and magnesium (71 g.)] in diethyl ether, at such a rate that vigorous reflux was maintained. The mixture was then heated at reflux for 40 hours and then treated with a saturated aqueous solution of ammonium chloride (3000 ml.). The ethereal layer was separated off and the aqueous layer was extracted with diethyl ether. The combined ethereal layers were dried over sodium sulphate, the solvent was removed in vacuo, and the residue distilled under reduced pressure to give methyl 3-iminovalerate (33 g.), b.p. 100°-120° C./20 mm Hg.

Workup

  1. customprepared by the method
  2. temperatureat such a rate that vigorous reflux
  3. temperaturewas maintained
  4. temperatureThe mixture was then heated
  5. temperatureat reflux for 40 hours
  6. customThe ethereal layer was separated off
  7. extractionthe aqueous layer was extracted with diethyl ether
  8. dry with materialThe combined ethereal layers were dried over sodium sulphate
  9. customthe solvent was removed in vacuo
  10. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-f3ca0219175e4b8cb7ea5f21d57b7e3d
Source dataset
uspto-grants-1977_06
Patent number
US04032323

Reaction notes

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