N-bromobutanimide → HCID 18446536, compound

HRID 1868319Notes

Reaction equation

HRID 1868319 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[S:6][CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][C:12]#[N:13].C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C>[Br:21][C:7]1[S:6][C:5]([CH2:4][CH2:3][CH2:2][OH:1])=[C:9]([CH2:10][CH2:11][C:12]#[N:13])[CH:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18446529HCID 18446529, compound

Product 1

HCID 18446536HCID 18446536, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[2-(3-hydroxy-propyl)-thiophen-3-yl]-propionitrile 83 (0.18 g, 0.9 mmol) in DMF (2 mL) was added NBS (0.18 g, 0.99 mmol). The mixture was then stirred at room temperature for 6 hours and then concentrated in vacuo. A solution of the residue in CH2Cl2 (80 mL) was washed with water, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (eluent: 50% EtOAc in hexane) afforded 84 (0.08 g). 1H NMR (400 MHz, d6-DMSO) δ: 7.06 (s, 1H), 4.53 (t, J=6.0 Hz, 1H), 3.41 (dd, J=6.0 and 11.5 Hz, 2H), 2.75 (m, 6H), 1.67 (m, 2H). MS (EI) m/z [(M+H+) (79Br)] 274, [(M+H+) (81Br)] 276, [(M−OH+) (79Br)] 256 and [(M−OH+) (81Br)] 258.

Workup

  1. concentrationconcentrated in vacuo
  2. washA solution of the residue in CH2Cl2 (80 mL) was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel column chromatography (eluent: 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-8278985b1af145228cf66829ea9cbc9d
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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