N-bromobutanimide → HCID 54283545, compound

HRID 441160Notes

Reaction equation

HRID 441160 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:9]=1[CH3:10])=[O:4].C1C(=O)N([Br:35])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O.CCCCCC.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([S:17]([CH3:20])(=[O:18])=[O:19])=[CH:15][CH:16]=2)[C:9]=1[CH2:10][Br:35])=[O:4]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 54294947HCID 54294947, compound

Product 1

HCID 54283545HCID 54283545, compoundYield 82.8%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of 404 mg of the product of Step 5, 200 mg of NBS, and 5 mg of benzoylperoxide in 10 mL of CCl4 was heated in a 80° C. oil bath under light from a W-lamp. After 30 min, the reaction mixture was cooled to room temperature, diluted with 10 mL of 3:1 EtOAc/hexane, and filtered through a pad of silica gel. The filtrate was concentrated in vacuo to give 400 mg of the crude title compound which was used for the next step without further purification.

Workup

  1. filtrationfiltered through a pad of silica gel
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fb05e088237c4c80b7a358b82bac5f54
Source dataset
uspto-grants-1996_05
Patent number
US05521213

Reaction notes

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