N-Iodosuccinimide → 7-Bromo-5-iodo-1,2,3-benzothiadiazol-4-amine
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:11])=[C:6]2[C:10]=1[S:9][N:8]=[N:7]2.C1C(=O)N([I:19])C(=O)C1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([I:19])[C:5]([NH2:11])=[C:6]2[C:10]=1[S:9][N:8]=[N:7]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 7-bromo-1,2,3-benzothiadiazol-4-amine (80.0 mg, 0.348 mmol) and NIS (117.3 mg, 0.522 mmol) in THF (6 ml) was stirred at RT overnight. The solution was adsorbed onto silica gel and purified by ISCO chromatography (10 to 30% EtOAc:heptane) to afford 95 mg (77%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 6.89 (s, 2 H), 8.05 (s, 1 H).
Workup
- custompurified by ISCO chromatography (10 to 30% EtOAc:heptane)
Sources & evidence
- ORD record
- ord-a725ace4fc094a08b3a9de8c26ac2396
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378104B2
Reaction notes
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