Acetic Acid → HCID 20477948, compound

HRID 904882Notes

Reaction equation

HRID 904882 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)[CH3:2].[C:11]([O:15][CH:16]([CH3:18])[CH3:17])(=[O:14])[CH:12]=[CH2:13].C(O)(=O)C>CCOCC>[CH2:1]([N:3]([CH2:13][CH2:12][C:11]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7603N-ethyl-3-methylanilineHCID 12716Isopropyl acrylate

Product 1

HCID 20477948HCID 20477948, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 13.5 g (0.1 mole) N-ethyl-m-toluidine, 11.4 g (0.1 mole) isopropyl acrylate and 2 ml glacial acetic acid was heated over the steam bath for 16 hours. The mixture was cooled and diluted with ether. The ether solution was washed with 10 ml water, twice with 10 ml portions of 5% sodium carbonate solution, once with 10 ml of water and then dried over sodium sulfate. Removal of the ether with a rotary evaporator at 50° C. and reduced pressure gave 22.0 g (86%) of oil, which was pure by thin layer chromatography and was used as isolated.

Workup

  1. temperaturewas heated over the steam bath for 16 hours
  2. temperatureThe mixture was cooled
  3. washThe ether solution was washed with 10 ml water, twice with 10 ml portions of 5% sodium carbonate solution, once with 10 ml of water
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the ether
  6. customwith a rotary evaporator at 50° C.

Sources & evidence

ORD record
ord-af05e4bb88224ac6b5f9f50eb5dad23a
Source dataset
uspto-grants-1983_12
Patent number
US04420555

Reaction notes

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