N-bromobutanimide → HCID 54283545, compound

HRID 2269575Notes

Reaction equation

HRID 2269575 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>[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

5

Reactant 2

HCID 67184N-bromobutanimideHCID 54294947HCID 54294947, compound

Product 1

HCID 54283545HCID 54283545, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 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 benzoylperoxde 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-80ffe694be0d48dd95174737ae5eb9e9
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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