Bromine → 4-(1,3-Benzothiazol-2-yl)-2-bromoaniline
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[Br:17]Br>C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][C:7]=1[Br:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
To a solution of 2-(4'-aminophenyl) benzothiazole (0.45 g, 1.99 mmol) in CH2Cl2 (50 ml) was added a solution of bromine (0.32 g, 1.99 mmol) in CH2Cl2 (10 ml) at -5° C. After the reaction mixture had been stirred still at -5° C. for 2 minutes, it was poured into ice-water (400 ml). The resulting mixture was stirred for 40 minutes at room temperature. The organic layer was separated, washed with 10% aqueous sodium thiosulfate (50 ml×2) and water (60 ml×2), dried (MgSO4) and concentrated. The residue was chromatographed on a silica gel column, eluting with ethyl acetate-hexane (1:3), to give pale yellow crystals (0.48 g, 79.1%), m.p. 160.0-161.4° C.
Workup
- stirringThe resulting mixture was stirred for 40 minutes at room temperature
- customThe organic layer was separated
- washwashed with 10% aqueous sodium thiosulfate (50 ml×2) and water (60 ml×2)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residue was chromatographed on a silica gel column
- washeluting with ethyl acetate-hexane (1:3)
Sources & evidence
- ORD record
- ord-9a70a4262c2e4008b66eead3c41c33dc
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06034246
Reaction notes
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