N-bromobutanimide → 1-(4-Bromomethyl-thiazol-2-yl)-ethanone

HRID 1178199Notes

Reaction equation

HRID 1178199 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7](=[O:9])[CH3:8])[S:5][CH:6]=1.C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:17][CH2:1][C:2]1[N:3]=[C:4]([C:7](=[O:9])[CH3:8])[S:5][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 53247972-Acetyl-4-methylthiazole

Product 1

HCID 692875611-(4-Bromomethyl-thiazol-2-yl)-ethanoneYield 72.6%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2a (4.38 g, 0.031 mol), NBS (5.8 g, 0.033 mol) and 100 mg of AIBN in 40 mL of carbon tetrachloride was heated at 70° C. for 16 h. Cooled to rt and the precipitate was filtered. The solvent was concentrated in vacuo to an oil that was subjected to flash chromatography (5% ethyl acetate/95% hexanes) to give 4.95 g (72%) of the desired product 3a. 1H NMR (CDCl3) δ 7.8 (s, 1H), 4.8 (s, 2H), 2.8 (s, 3H).

Workup

  1. filtrationthe precipitate was filtered
  2. concentrationThe solvent was concentrated in vacuo to an oil that

Sources & evidence

ORD record
ord-dae199b9f0c14a65bc664c466cfff4e4
Source dataset
uspto-grants-2007_10
Patent number
US07276502B2

Reaction notes

Loading…