Tert-Butyl nitrite → 7-Bromo-5-iodo-1,2,3-benzothiadiazole

HRID 389482Notes

Reaction equation

HRID 389482 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([I:12])[C:5](N)=[C:6]2[C:10]=1[S:9][N:8]=[N:7]2.N(OC(C)(C)C)=O>C1COCC1>[Br:1][C:2]1[C:10]2[S:9][N:8]=[N:7][C:6]=2[CH:5]=[C:4]([I:12])[CH:3]=1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 667596527-Bromo-5-iodo-1,2,3-benzothiadiazol-4-amine

Product 1

HCID 667608087-Bromo-5-iodo-1,2,3-benzothiadiazoleYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-bromo-5-iodo-1,2,3-benzothiadiazol-4-amine (95 mg, 0.267 mmol) in THF (6 mL) was added tert-butyl nitrite (0.127 mL, 1.067 mmol) at RT, and the reaction was stirred for 30 min. The solution was adsorbed onto silica gel and purified by ISCO chromatography (1% EtOAc:heptane) to afford 55 mg (60%) of the title compound as a brown solid. 1H NMR (400 MHz, CDCl3): δ 8.09 (d, J=1.0 Hz, 1 H), 8.94 (d, J=1.3 Hz, 1 H).

Workup

  1. custompurified by ISCO chromatography (1% EtOAc:heptane)

Sources & evidence

ORD record
ord-b1ad48a280c945cfa00f4667ae3abc4b
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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