N-bromobutanimide → HCID 57634238, compound

HRID 2109430Notes

Reaction equation

HRID 2109430 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]1[CH2:10][C:9]2([CH:15]3[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]3)[CH2:11]2)[O:8][C:7]1=[O:18].[Br:19]N1C(=O)CCC1=O>CN(C)C=O.C(Cl)(Cl)Cl>[Br:19][C:5]1[S:1][C:2]([N:6]2[CH2:10][C:9]3([CH:15]4[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]4)[CH2:11]3)[O:8][C:7]2=[O:18])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 576342333'-(1,3-Thiazol-2-yl)-2'H-spiro[4-azabicyclo[2.2.2]octane-2,5'-[1,3]oxazolidin]-2'-one

Product 1

HCID 57634238HCID 57634238, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution containing 3′-(thiazol-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one (2.80 g, 10.55 mmol) and N-bromosuccinimide (3.90 g, 21.86 mmole) in N,N-dimethylformamide (15 mL) were stirred at RT overnight. The mixture was diluted with chloroform, washed with saturated aqueous potassium carbonate and then with brine, dried through magnesium sulfate, and then the solvent was evaporated. The residue was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give the title compound as a pale solid (1.70 g), m/z 343, 345 (MH+).

Workup

  1. washwashed with saturated aqueous potassium carbonate
  2. dry with materialwith brine, dried through magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-542382f54e8c44d985f481df8ef91b7e
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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