Benzoyl Peroxide → 5-Bromomethyl-2-methylbenzothiazole
Reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:5]=2[N:6]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
8.16 g of 2,5-dimethylbenzothiazole was dissolved in 50 ml of carbon tetrachloride. To the solution were added 8.9 g of N-bromosuccinimide and 82 mg of benzoyl peroxide. The mixture was refluxed for 3 hours. The resulting insolubles were removed by filtration. The solvent of the filtrate was removed by distillation under reduced pressure to obtain 5-bromomethyl-2-methylbenzothiazole. It was suspended in 100 ml of 50% acetic acid. To the suspension was added 14.00 g of hexamethylenetetramine, and the mixture was refluxed for 1 hour. The reaction mixture was mixed with 200 ml of water. The resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: n-hexane/ethyl acetate=3/1) to obtain 3.54 g of colorless crystals of 2-methyl-5-formylbenzothiazole having a melting point of 92°-94° C.
Workup
- temperatureThe mixture was refluxed for 3 hours
- customThe resulting insolubles were removed by filtration
- customThe solvent of the filtrate was removed by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-18a029a708c64229b31605e1aa46a64a
- Source dataset
- uspto-grants-1990_08
- Patent number
- US04948796
Reaction notes
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