Aniline → HCID 178450488, compound

HRID 1382353Notes

Reaction equation

HRID 1382353 reaction equation
[C:1]([C:6](=[CH:12]OCC)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[C:1]([C:6](=[CH:12][NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 6115AnilineHCID 3359484Ethyl 2-butyryl-3-ethoxyacrylate

Product 1

HCID 178450488HCID 178450488, compoundYield 68.9%

Procedure

A mixture of ethyl 2-butyryl-3-ethoxyacrylate (95 g, 0.4 mol) and aniline (36 ml, 0.4 mol) was heated at reflux for 30 minutes, then cooled, diluted with petroleum ether, and left to crystallise at -20° overnight. Filtration and washing gave ethyl 2-butyryl-3-(phenylamino)acrylate (72 g, 60%) as a mixture of E and Z isomers.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. temperaturecooled
  4. waitleft
  5. customto crystallise at -20° overnight
  6. filtrationFiltration
  7. washwashing

Sources & evidence

ORD record
ord-9747905eccda4984832de45e2f37c7b3
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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