Benzoyl chloride → HCID 178471920, compound

HRID 1382322Notes

Reaction equation

HRID 1382322 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[C:19]([C:13](=[CH:12][NH:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH3:3])[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 67899433Ethyl3-(2-methoxyphenylamino)acrylate

Product 1

HCID 178471920HCID 178471920, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
5 °C

Procedure

50% Sodium hydride (2.4 g, 0.05 mol) was washed with petroleum ether, suspended in dry toluene (50 ml) and stirred at 5° C. Ethyl 3-(2-methoxyphenylamino)acrylate (8.7 g, 0.05 mol) in dry toluene (25 ml) was added and the mixture was stirred for 2.5 hours. Benzoyl chloride (6.8 g, 0.05 mol) in dry toluene (25 ml) was added dropwise and the mixture was heated under reflux for 2 hours. The mixture was cooled, washed with dilute hydrochloric acid, water and brine, then dried and evaporated. The residue was chromatographed (silica gel, dichloromethane) to afford ethyl 2-benzoyl-3-(2-methoxyphenylamino)acrylate (7.62 g, 46.8%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred for 2.5 hours
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. temperatureThe mixture was cooled
  5. washwashed with dilute hydrochloric acid, water and brine
  6. customdried
  7. customevaporated
  8. customThe residue was chromatographed (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-112cdb9fcec24578a86ff4bb3d0e24cf
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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