p-Anisoyl chloride → HCID 178450486, compound

HRID 1534462Notes

Reaction equation

HRID 1534462 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][OH:21])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4].[C:22](Cl)(=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1>N1C=CC=CC=1>[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 178450487HCID 178450487, compound

Product 1

HCID 178450486HCID 178450486, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 2-butyryl-3-(2-(hydroxymethyl)phenylamino)-acrylate (14.6 g, 50 mmol) was dissolved in pyridine (50 ml), cooled in ice, and p-anisoyl chloride (12.8 g, 75 mmol), added dropwise. The mixture was stirred 16 hours with warming to room temperature, then evaporated, taken up in dichloromethane, washed with aqueous sodium bicarbonate, dried and evaporated. Crystallization from ether gave ethyl 2-butyryl-3-(2-(4-methoxybenzoyloxymethyl)phenylamino)acrylate (12.3 g, 58%).

Workup

  1. temperaturecooled in ice
  2. customevaporated
  3. washwashed with aqueous sodium bicarbonate
  4. customdried
  5. customevaporated
  6. customCrystallization from ether

Sources & evidence

ORD record
ord-e63469d2f3084615b57427bce8e5bfc7
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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