N-bromobutanimide → 2-(Bromomethyl)-5-methoxy-1,3-benzothiazole
Reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[S:11][C:12]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:13]=2[N:14]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[S:11][C:12]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:13]=2[N:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2.58 g (14.5 mmol; 1.3 eq.) of N-bromosuccinimide and a spatula tip's worth of aza-bis-isobutyronitrile are added to 2 g (11.16 mmol) of 2-methyl-5-methoxy-1,3-benzothiazole in solution in 25 ml of anhydrous carbon tetrachloride. The reaction mixture is heated under reflux and under irradiation for 6 hours, with a spatula tip's worth of aza-bis-isobutyronitrile added every 2 hours. After returning to ambient temperature, the insoluble part formed is filtered, the solvent is evaporated off under reduced pressure and the residue is purified by chromatography on a silica column (eluent: ethyl acetate/heptane 1/4). The expected product is obtained in the form of a white solid.