Diethyl bromomalonate → HCID 20477379, compound

HRID 905122Notes

Reaction equation

HRID 905122 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.Br[CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([N:6]([CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69637Diethyl bromomalonateHCID 702724-Chloro-N-methylbenzenamine

Product 1

HCID 20477379HCID 20477379, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Chloro-N-methylaniline (10.1 g), diethyl bromomalonate (8.5 g) and dry benzene (60 ml) were mixed, and heated under reflux for 7 hours with stirring. The reaction mixture was washed, dried and concentrated by the same procedure as in Example 2, (1). The residue was chromatographed on a silica gel column using benzene/hexane (1:1) as an eluent to give 3.5 g (yield 33%) of diethyl p-chloro-N-methylanilinomalonate having the following NMR data.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 7 hours
  3. washThe reaction mixture was washed
  4. customdried
  5. concentrationconcentrated by the same procedure as in Example 2, (1)
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-1829782760b449ffa0d6c8a8eb1ef91c
Source dataset
uspto-grants-1983_12
Patent number
US04421914

Reaction notes

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