N-bromobutanimide → HCID 68494779, compound

HRID 2381780Notes

Reaction equation

HRID 2381780 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([Br:17])=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 7945658HCID 7945658, compound

Product 1

HCID 68494779HCID 68494779, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-benzyl-3-methylthiophene-2-carboxamide (6.63 g, 28.66 mmol) and N-bromosuccinimide (5.10 g, 28.66 mmol) in anhydrous acetonitrile (70 mL) was stirred at ambient temperature for 18 h, and diluted with ethyl acetate (200 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (4×100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with ethyl acetate/hexanes to afford the title compound as a colorless solid (6.48 g, 73%): 1H NMR (300 MHz, CDCl3) δ 7.40-7.29 (m, 5H), 6.87 (s, 1H), 5.95 (br s, 1H), 4.59 (d, J=5.7 Hz, 2H), 2.47 (s, 3H); MS (ES+) m/z 310.2 (M+1), 312.2 (M+1).

Workup

  1. washThe organic layer was washed with saturated aqueous sodium bicarbonate (4×100 mL) and brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0c70c8216033407ea66645cad985a3cb
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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