Water → Ethyl 3-(acryloylamino)benzoate

HRID 862418Notes

Reaction equation

HRID 862418 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[NH2:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11].O>CC(C)=O>[C:1]([NH:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 11400Ethyl 3-aminobenzoateHCID 13140Acryloyl chloride

Product 1

HCID 15157146Ethyl 3-(acryloylamino)benzoateYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Propenoyl chloride (668 mg, 600 ul, 7.4 mMole) was added dropwise to an ice-cold solution of ethyl 3-aminobenzoate (2.0 gm, 12 mMole) in 10 ml of acetone. The solution was stirred for 30 minutes on ice and then for 30 minutes at room temperature. 50 ml of water was added and the yellowish oil was separated by decantation. It was washed with water and then dissolved in 15 ml of diethl ether. This solution was washed with 10% (w/v) sodium bicarbonate, water and then dried over anhydrous sodium carbonate. The ether was evaporated and a white creamy product was crystallized from ethanol. The overall yield was 37%, and the melting point of the product was 93° C. to 94° C.

Workup

  1. waitfor 30 minutes at room temperature
  2. customthe yellowish oil was separated by decantation
  3. washIt was washed with water
  4. dissolutiondissolved in 15 ml of diethl ether
  5. washThis solution was washed with 10% (w/v) sodium bicarbonate, water
  6. dry with materialdried over anhydrous sodium carbonate
  7. customThe ether was evaporated
  8. customa white creamy product was crystallized from ethanol
  9. customwas 93° C. to 94° C.

Sources & evidence

ORD record
ord-7e83e424cb394919970f29a856bd5410
Source dataset
uspto-grants-1998_02
Patent number
US05719151

Reaction notes

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