N-bromobutanimide → HCID 58370163, compound

HRID 2062129Notes

Reaction equation

HRID 2062129 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][N:5]=1)=[O:3].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:18][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([S:2]([CH3:1])=[O:3])=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22087242HCID 22087242, compound

Product 1

HCID 58370163HCID 58370163, compoundYield 28.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 0.33 g of 2-methanesulfinyl-5-methyl-pyridine in 20 mL of carbon tetrachloride was added 0.40 g NBS and 6 mg benzoyl peroxide. This mixture was refluxed for 4 hours. The reaction mixture was cooled to room temperature, washed with aqueous sodium hydrogen carbonate solution, dried over sodium sulphate, and concentrated to dryness. Purification by flash chromatography (silica, heptane/ethyl acetate) provided 0.14 g of 5-bromomethyl-2-methanesulfinyl-pyridine.

Workup

  1. temperatureThis mixture was refluxed for 4 hours
  2. washwashed with aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated to dryness
  5. customPurification by flash chromatography (silica, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-94cba76360bf4e40a4618d15815b5dad
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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