N-bromobutanimide → HCID 58370234, compound

HRID 2075562Notes

Reaction equation

HRID 2075562 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][N:6]=1)(=[O:4])=[O:3].[Br:12]CC1C=CC(S(C)=O)=NC=1.C1C(=O)N(Br)C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 234370392-(Methanesulfonyl)-5-methylpyridineHCID 58370163HCID 58370163, compound

Product 1

HCID 58370234HCID 58370234, compound

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 0.25 g of 2-methanesulfonyl-5-methyl-pyridine (from the preparation of 5-bromomethyl-2-methanesulfinyl-pyridine, step b)) in 20 mL carbon tetrachloride was added 0.27 g NBS and 4 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 0.11 g of 5-bromomethyl-2-methanesulfonyl-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-7d613228cb4246c792ef02193f3ee4e6
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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