N-bromobutanimide → HCID 131717797, compound

HRID 258027Notes

Reaction equation

HRID 258027 reaction equation
[CH2:1]([O:4][C:5]1[C:13]2[O:12][CH:11]([C:14]([O:16][CH2:17]C)=[O:15])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)[C:2]#[CH:3].C1C(=O)N([Br:26])C(=O)C1>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:26][C:3]#[C:2][CH2:1][O:4][C:5]1[C:13]2[O:12][CH:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 131717796HCID 131717796, compound

Product 1

HCID 131717797HCID 131717797, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

67.98 g (0.293 mol) of the compound from Example 46 and 61 g (0.340 mol) of NBS are stirred at 20° C. for 30 minutes in the presence of 5 g of AgNO3 in 2.5 l of acetone. The mixture is concentrated to about 500 ml, poured onto 2 l of ice/water and shaken twice with 500 ml of ethyl acetate each time. The mixture is filtered, and the ethyl acetate phases are dried over Na2SO4 and evaporated. The residue is flash chromatographed on silica gel (eluent: petroleum ether/acetone 3:1).

Workup

  1. concentrationThe mixture is concentrated to about 500 ml
  2. additionpoured onto 2 l of ice/water
  3. filtrationThe mixture is filtered
  4. dry with materialthe ethyl acetate phases are dried over Na2SO4
  5. customevaporated
  6. customchromatographed on silica gel (eluent: petroleum ether/acetone 3:1)

Sources & evidence

ORD record
ord-cfe355a5fb4b46d792681d2c07a919ae
Source dataset
uspto-grants-1993_11
Patent number
US05264458

Reaction notes

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