Water → HCID 45095769, compound

HRID 2094796Notes

Reaction equation

HRID 2094796 reaction equation
O1CCOCC1.[CH2:7]([C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[CH2:16])=[N:13][CH:14]=1)[CH3:8].[Br:17]N1C(=O)CCC1=O.[OH2:25]>>[Br:17][CH2:16][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([CH2:7][CH3:8])=[CH:14][N:13]=1)[OH:25]

Participants

5

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 67184N-bromobutanimideHCID 222462Pyridine, 5-ethyl-2-vinyl-

Product 1

HCID 45095769HCID 45095769, compoundYield 85%

Conditions

Temperature
27.5 °C

Procedure

To a stirred mixture of 225 mL 1,4-dioxane and 225 mL water, 75 g (0.5639 mol) of 5-ethyl-2-vinyl-pyridine was added, followed by 149 g (0.8371 mol) N-bromosuccinimide was added in to it. Reaction mixture was stirred at 25-30° C. for 4 hr. and subsequently quenched with excess water. Product was extracted with dichloromethane. Organic layer was separated and dried over calcium chloride. On concentrating the organic layer and purifying the residue, it gave 110.24 g (85%) of desired product.

Workup

  1. additionwas added
  2. additionwas added in to it
  3. customReaction mixture
  4. customand subsequently quenched with excess water
  5. extractionProduct was extracted with dichloromethane
  6. customOrganic layer was separated
  7. dry with materialdried over calcium chloride
  8. concentrationOn concentrating the organic layer
  9. custompurifying the residue, it

Sources & evidence

ORD record
ord-2e5f73fd7c564ab29cdf5e554982aed0
Source dataset
uspto-grants-2013_05
Patent number
US08445685B2

Reaction notes

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