Methacryloyl chloride → HCID 89880870, compound

HRID 2201672Notes

Reaction equation

HRID 2201672 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].C(=O)([O-])O.[Na+].[C:18](Cl)(=[O:22])[C:19]([CH3:21])=[CH2:20]>O.C(OCC)(=O)C>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:18](=[O:22])[C:19]([CH3:21])=[CH2:20])=[CH:11][CH:12]=1)([O-:4])=[O:3]

Participants

6

Reactant 3

HCID 13528Methacryloyl chlorideHCID 516892Sodium BicarbonateHCID 112524674-Nitrobenzylamine hydrochloride

Product 1

HCID 89880870HCID 89880870, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitrobenzylamine hydrochloride (1.51 g) and sodium hydrogencarbonate (4.13 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 (1.26 g) was added dropwise thereto. After stirring for 10 minutes, the mixture was extracted with ethyl acetate. After washing with water and brine, the organic layer was dried over anhydrous sodium sulfate and evaporated. After that, the recrystallization was performed by using a mixture solvent of hexane and ethyl acetate. N-(4-Nitrobenzyl)methacrylamide was obtained as pale yellowish crystals. The yield was 1.05 g (60%). 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. extractionthe mixture was extracted with ethyl acetate
  4. washAfter washing with water and brine
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customevaporated
  7. customAfter that, the recrystallization

Sources & evidence

ORD record
ord-b00f862da8cb4ba0b9d3de9f64124d51
Source dataset
uspto-grants-2016_06
Patent number
US09365501B2

Reaction notes

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