N-bromobutanimide → HCID 19101519, compound

HRID 1974439Notes

Reaction equation

HRID 1974439 reaction equation
[C:1](=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:5]([O:7][CH3:8])=[O:6])([CH3:3])[CH3:2].C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[C:1](=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:5]([O:7][CH2:8][Br:20])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5162084Dimethyl (propan-2-ylidene)propanedioate

Product 1

HCID 19101519HCID 19101519, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 26. 4 grams (0.15 mol) of dimethyl isopropylidenemalonate and 27.5 grams (0.15 mol) of n-bromosuccinimide were stirred in 150 mL carbon tetrachloride containing 1.0 grams benzoyl peroxide. The mixture was refluxed for 16 hours under nitrogen. The reaction was cooled in ice and the succinimide was filtered off and washed with carbon tetrachloride. The solvent was removed under reduced pressure to yield 41.3 grams of impure bromomethyl methyl isopropylidenemalonate as an oil which was used without further purification.

Workup

  1. temperatureThe mixture was refluxed for 16 hours under nitrogen
  2. temperatureThe reaction was cooled in ice
  3. filtrationthe succinimide was filtered off
  4. washwashed with carbon tetrachloride
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d858b7c4856443bf821a86446567fecc
Source dataset
uspto-grants-1994_02
Patent number
US05283165

Reaction notes

Loading…