Water → HCID 45095769, compound

HRID 1922035Notes

Reaction equation

HRID 1922035 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[CH2:10])=[N:7][CH:8]=1)[CH3:2].[Br:11]N1C(=O)CCC1=O.[OH2:19]>CS(C)=O>[Br:11][CH2:10][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][N:7]=1)[OH:19]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 222462Pyridine, 5-ethyl-2-vinyl-

Product 1

HCID 45095769HCID 45095769, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution at −5° C., of 50 g (0.3759 mol) 5-ethyl-2-vinyl-pyridine dissolved in a mixture of 2504 mL dimethylsulfoxide and 13.5 mL water was added 99.3 g (0.5578 mole) N-bromosuccinimide and stirring was continued for 30 min. at 0 to −5° C. Reaction mixture was quenched with 2500 mL water and the product was extracted with dichloromethane. Organic layer was dried (calcium chloride); concentrated and purified to get the desired product. Yield of the product was 76.09 g (88%). The two side products in this reaction found were 2-acetyl-5-ethyl-pyridine (5%) and 2-(1-bromo vinyl)-5-ethyl-pyridine (6%).

Workup

  1. customReaction mixture
  2. customwas quenched with 2500 mL water
  3. extractionthe product was extracted with dichloromethane
  4. dry with materialOrganic layer was dried (calcium chloride)
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-6891c19038664e3fb8cf890e88c98124
Source dataset
uspto-grants-2012_05
Patent number
US08173816B2

Reaction notes

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