Methyl iodide → N-methyl-N-(3-bromophenyl)-3,3-dimethyl-acrylamide

HRID 37406Notes

Reaction equation

HRID 37406 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:16])[CH:12]=[C:13]([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1.[CH3:17]I>CS(C)=O>[CH3:17][N:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([Br:3])[CH:5]=1)[C:11](=[O:16])[CH:12]=[C:13]([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 19177475N-3,3-Dimethylacryloyl-3-bromoaniline

Product 1

HCID 19935491N-methyl-N-(3-bromophenyl)-3,3-dimethyl-acrylamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

28.7 g of powdered potassium hydroxide were suspended in 300 ml of dimethyl sulfoxide and a solution of 32.6 g of N-(3-bromophenyl)-3,3-dimethyl-acrylamide in 200 ml of dimethylsulfoxide (DMSO) was added dropwise thereto. The mixture was stirred at room temperature for 30 minutes and subsequently a solution of 27.5 g of methyl iodide in 150 ml of DMSO was added dropwise thereto. After 2.5 hours the mixture was poured on to 1 l of ice/water and extracted with ethyl acetate. The organic phase was washed repeatedly with water, dried and evaporated. The oily residue was distilled in a high vacuum. There were obtained 29.3 g of N-methyl-N-(3-bromophenyl)-3,3-dimethyl-acrylamide as a slightly yellow oil, boiling point 112°-114° C./67 Pa.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed repeatedly with water
  3. customdried
  4. customevaporated
  5. distillationThe oily residue was distilled in a high vacuum

Sources & evidence

ORD record
ord-367247f261d14671948eac48ee6f1733
Source dataset
uspto-grants-1995_05
Patent number
US05420273

Reaction notes

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