N-bromobutanimide → HCID 22279872, compound

HRID 2086181Notes

Reaction equation

HRID 2086181 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]([CH3:16])([CH2:9][CH2:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[CH2:7][OH:8])=[O:4].[Br:17]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][O:2][C:3]([NH:5][C:6]([CH3:16])([CH2:9][CH2:10][C:11]1[S:12][C:13]([Br:17])=[CH:14][CH:15]=1)[CH2:7][OH:8])=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22279870HCID 22279870, compound

Product 1

HCID 22279872HCID 22279872, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methoxycarbonylamino-2-methyl-4-(2-thienyl)butan-1-ol (11.7 g, 48.0 mmol) obtained in Example 1(d) was dissolved in dimethylformamide (120 ml), and N-bromosuccinimide (10.8 g, 60.8 mmol) was added thereto in an ice bath followed by stirring for 4 hours at room temperature under a nitrogen atmosphere. The reaction mixture was poured into ice-cold 10% hydrochloric acid (300 ml), and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was concentrated in vacuo, and the residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=4:1-1:3); to afford the title compound (12.4 g, 80% yield) as a pale yellow oil.

Workup

  1. customin an ice bath followed
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated in vacuo
  6. customthe residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=4:1-1:3)

Sources & evidence

ORD record
ord-eb67df317e764af68dcefd1d309497ae
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

Loading…