Methacryloyl chloride → HCID 89880894, compound

HRID 2201670Notes

Reaction equation

HRID 2201670 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH2:13])=[CH:7][CH:6]=1)([O-:4])=[O:3].C(=O)([O-])O.[Na+].[C:19](Cl)(=[O:23])[C:20]([CH3:22])=[CH2:21]>O.C(OCC)(=O)C>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][NH:13][C:19](=[O:23])[C:20]([CH3:22])=[CH2:21])=[CH:9][CH:10]=1)([O-:4])=[O:3]

Participants

6

Reactant 3

HCID 13528Methacryloyl chlorideHCID 458983Benzeneethanamine, 4-nitro-, hydrochloride (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 89880894HCID 89880894, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Nitrophenyl)ethylamine hydrochloride (1.72 g) and sodium hydrogencarbonate (5.00 g) were dissolved in water (25 mL), to which ethyl acetate (25 mL) was added, followed by being stirred in an ice bath. Methacryloyl chloride (1.79 g) was added dropwise thereto. After stirring for 10 minutes, the organic layer was separated. The aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with water and brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The recrystallization was performed by using a mixture solvent of hexane and ethyl acetate. N-[2-(4-Nitrophenyl)ethyl]methacrylamide was obtained as pale yellowish crystals. The yield was 1.25 g (63%). Spectrum data of 1H-NMR (400 MHz, CDCl3) is shown for the obtained compound.

Workup

  1. additionwas added
  2. stirringAfter stirring for 10 minutes
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe recrystallization

Sources & evidence

ORD record
ord-a11db63021ac408ca32e6ee75de6c4b5
Source dataset
uspto-grants-2016_06
Patent number
US09365501B2

Reaction notes

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