N-Iodosuccinimide → 7-Bromo-5-iodo-1,2,3-benzothiadiazol-4-amine

HRID 389481Notes

Reaction equation

HRID 389481 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]2

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 667604377-Bromo-1,2,3-benzothiadiazol-4-amine

Product 1

HCID 667596527-Bromo-5-iodo-1,2,3-benzothiadiazol-4-amineYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. 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

Loading…