Water → 2-[Methyl(4-nitrophenyl)amino]ethyl 2-methylprop-2-enoate

HRID 1590532Notes

Reaction equation

HRID 1590532 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([N:16]([CH2:18][CH2:19][OH:20])[CH3:17])=[CH:12][CH:11]=1)([O-:9])=[O:8].N1C=CC=CC=1.O>C(Cl)(Cl)Cl>[C:1]([O:20][CH2:19][CH2:18][N:16]([C:13]1[CH:12]=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:15][CH:14]=1)[CH3:17])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 13528Methacryloyl chlorideHCID 45470772-(Methyl(4-nitrophenyl)amino)ethan-1-ol

Product 1

HCID 539427282-[Methyl(4-nitrophenyl)amino]ethyl 2-methylprop-2-enoateYield 38.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2.67 g of methacryloyl chloride in 5 ml of chloroform were added dropwise to 5 g of 2-[N-(p-nitrophenyl)-N-methylamino]-ethanol and 2.02 g of pyridine in 40 ml of chloroform while cooling. Thereafter, the resulting reaction solution was first stirred at room temperature and then refluxed for 3.5 hours. It was cooled to room temperature and then 40 ml of water were added to it, after which the chloroform phase was separated off and the aqueous phase was extracted with three times 20 ml of chloroform. After the combined chloroform phases had been dried with Na2SO4 and the chloroform evaporated off, the resulting product was washed with hexane and dried under reduced pressure. 2.6 g of 2-[N-(p-nitrophenyl)-N-methylamino]-ethyl methacrylate were obtained, the IR spectrum of the product in the form of a KBr pellet having bands at 2,950, 2,900, 1,720, 1,600, 1,510, 1,490, 1,320, 1,310, 1,160, 1,110 and 825 cm-1.

Workup

  1. temperaturewhile cooling
  2. customThereafter, the resulting reaction solution
  3. temperaturerefluxed for 3.5 hours
  4. temperatureIt was cooled to room temperature
  5. customafter which the chloroform phase was separated off
  6. extractionthe aqueous phase was extracted with three times 20 ml of chloroform
  7. dry with materialAfter the combined chloroform phases had been dried with Na2SO4
  8. customthe chloroform evaporated off
  9. washthe resulting product was washed with hexane
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-a6565b38c15d4d3e98ff11ee14b8667c
Source dataset
uspto-grants-1993_04
Patent number
US05204178

Reaction notes

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