N-bromobutanimide → HCID 9822596, compound

HRID 1737649Notes

Reaction equation

HRID 1737649 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].C1C(=O)N([Br:29])C(=O)C1>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:29])[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-bromosuccimide. 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-4973688f20ef48739304649393e49b57
Source dataset
uspto-grants-1999_10
Patent number
US05962481

Reaction notes

Loading…