3-Chloro-2-methyl-1-propene → N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-en-1-yl)acetamide

HRID 546565Notes

Reaction equation

HRID 546565 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[NH:13][C:14](=[O:16])[CH3:15].Cl[CH2:18][C:19]([CH3:21])=[CH2:20]>CN(C)C=O.O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[N:13]([CH2:20][C:19]([CH3:21])=[CH2:18])[C:14](=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 21959509N-(2-Bromo-5-nitrophenyl)acetamide

Product 1

HCID 21959573N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-en-1-yl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of 1.34 g of sodium hydride in 10 mL of dimethylformamide under argon is added dropwise, at 0° C., a solution of 5.8 g of N-(2-bromo-5-nitrophenyl)acetamide obtained in stage c) below in 90 mL of dimethylformamide and the reaction medium is stirred at this temperature for 1 hour. 3.3 mL of 3-chloro-2-methylprop-1-ene are then added and the mixture is then heated at 60° C. for 2 hours. After cooling to room temperature, the mixture is diluted with one litre of water and extracted with four times 80 mL of ethyl acetate. The combined organic phases are washed with three times 50 mL of saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of heptane and ethyl acetate (80/20 by volume) to give 5.2 g of N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-en-1-yl)acetamide in the form of a yellow solid, the characteristics of which are as follows:

Workup

  1. additionis added dropwise, at 0° C.
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with four times 80 mL of ethyl acetate
  4. washThe combined organic phases are washed with three times 50 mL of saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by chromatography on a column of silica
  9. washeluting with a mixture of heptane and ethyl acetate (80/20 by volume)

Sources & evidence

ORD record
ord-8e99596bd2c54f5eafa32b9be4e3eaf3
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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