Aniline → HCID 19101520, compound

HRID 1974440Notes

Reaction equation

HRID 1974440 reaction equation
[C:1](=[C:4]([C:10]([O:12]C)=O)[C:5]([O:7][CH2:8]Br)=[O:6])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH3:8][O:7][C:5]([C:4]1[C:10](=[O:12])[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:2][C:1]=1[CH3:3])=[O:6]

Participants

4

Reactant 2

HCID 6115AnilineHCID 19101519HCID 19101519, compound

Product 1

HCID 19101520HCID 19101520, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 20.6 grams (82 mmol) of impure bromomethyl methyl isopropylidenemalonate and 15.2 grams (0.169 mol) of aniline in 25 mL of absolute ethanol were stirred at room temperature. Initially a homogeneous solution formed. After a mildly exothermic reaction a precipitate formed. The reaction was refluxed for 1 hour, cooled, and filtered. The collected product was washed with ethanol and water to give 10.0 grams (43 mmol, 52% yield) of crude product. An analytical sample was prepared by recrystallizing from methanol, m. p.=143°-145° C., Elemental Analysis: Calculated: C=67.5, H=5.7, N=6.1; Found: C=67.7, H=5.9, N=6.2.

Workup

  1. customInitially a homogeneous solution formed
  2. customAfter a mildly exothermic reaction a precipitate
  3. customformed
  4. temperatureThe reaction was refluxed for 1 hour
  5. temperaturecooled
  6. filtrationfiltered
  7. washThe collected product was washed with ethanol and water

Sources & evidence

ORD record
ord-ef637a57a1684c298c7f789393a42c77
Source dataset
uspto-grants-1994_02
Patent number
US05283165

Reaction notes

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