N-bromobutanimide → HCID 9822596, compound

HRID 1530910Notes

Reaction equation

HRID 1530910 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:8][S:7][CH:6]=1)=[O:4].[Br:22]N1C(=O)CCC1=O>CC(O)=O.C(Cl)(Cl)Cl.CCOCC>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:8]([Br:22])[S:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 3542677HCID 3542677, compound

Product 1

HCID 9822596HCID 9822596, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21584526Acetic acid chloroformSolvent

Procedure

To a solution of the product of Example 2 in 5.0 mL of AcOH-CHCl3 (1:1) at room temperature was added 0.299 g (1.682 mmol) of N-bromosuccinimide. The reaction was stirred for 18 h and then diluted with ether, washed with water and saturated sodium bicarbonate solution, dried over MgSO4, filtered and concentrated in vacuo. The tan solid residue was washed with ether-hexanes (1:1) to provide 0.504 g (81%) of the desired product as a tan solid. Electrospray Mass Spec:406.1 (M+H)+

Workup

  1. washwashed with water and saturated sodium bicarbonate solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe tan solid residue was washed with ether-hexanes (1:1)

Sources & evidence

ORD record
ord-5cd76b98a56a4783ad669611f7ccc8e0
Source dataset
uspto-grants-2001_03
Patent number
US06197795B1

Reaction notes

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