N-bromobutanimide → HCID 68494779, compound

HRID 1887237Notes

Reaction equation

HRID 1887237 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>[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

4

Reactant 2

HCID 67184N-bromobutanimideHCID 7945658HCID 7945658, compound

Product 1

HCID 68494779HCID 68494779, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of N-benzyl-3-methylthiophene-2-carboxamide (0.74 g, 3.18 mmol) in acetonitrile (15 mL) was added N-bromosuccinimide (0.57 g, 3.18 mmol). The reaction mixture was stirred for 16 h, and then concentrated in vacuo. The residue was purified by column chromatography eluting with 5-35% ethyl acetate in hexane to afford the title compound as a colorless solid (0.69 g, 69%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.30 (m, 5H), 6.87 (s, 1H), 4.59 (d, J=5.6 Hz, 2H), 2.46 (s, 3H); MS (ES+) m/z 310.1 (M+1), 312.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography
  3. washeluting with 5-35% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1d3a0f9c914c4b669b996a5c629e5a5b
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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