N-bromobutanimide → HCID 9822596, compound

HRID 1275582Notes

Reaction equation

HRID 1275582 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>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

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3542677HCID 3542677, compound

Product 1

HCID 9822596HCID 9822596, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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-cca1a79255cc41fcb0cf7c0ca93f6966
Source dataset
uspto-grants-2000_12
Patent number
US06162814

Reaction notes

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