N-bromobutanimide → HCID 10594137, compound

HRID 2393098Notes

Reaction equation

HRID 2393098 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:20][C:12]1[CH:11]=[CH:10][C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16]([CH3:19])=[N:17]2

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 656671Sodium PyrosulfiteHCID 15769668HCID 15769668, compound

Product 1

HCID 10594137HCID 10594137, compoundYield 138.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-bromosuccinimde (14 g) was added in one portion to a stirred solution of 8-t-butyldimethylsilyloxyquinaldine (15 g) in chloroform at -40° C. under an inert atmosphere. The reaction was warmed to room temperature and then heated to reflux for 6 h. Further N-bromosuccinimide (6 g) was added to the reaction at room temperature and stirring continued for 3 days. The reaction mixture was poured into 5% aqueous sodium metabisulphite solution (300 ml) and extracted with chloroform (3×300 ml). The combined organic phases were dried over magnesium sulphate and concentrated in vacuo to afford the title compound as an orange oil (16.4 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 h
  3. extractionextracted with chloroform (3×300 ml)
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d599f814d72b4615955f4840ba700e9b
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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