N-bromobutanimide → 7-Bromo-1,2,3-benzothiadiazol-4-amine

HRID 389480Notes

Reaction equation

HRID 389480 reaction equation
[S:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([NH2:10])=[C:4]2[N:3]=[N:2]1.C1C(=O)N([Br:18])C(=O)C1>C1COCC1>[Br:18][C:6]1[CH:7]=[CH:8][C:9]([NH2:10])=[C:4]2[C:5]=1[S:1][N:2]=[N:3]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21936630benzo[d][1,2,3]thiadiazol-4-aMine

Product 1

HCID 667604377-Bromo-1,2,3-benzothiadiazol-4-amineYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,2,3-benzothiadiazol-4-amine (200.0 mg, 1.323 mmol) and NBS (341.4 mg, 1.918 mmol) in THF (10 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 80 mg (30%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 6.74 (d, J=8.3 Hz, 1 H), 6.97 (s, 2 H), 7.60 (d, J=8.3 Hz, 1 H).

Workup

  1. custompurified by ISCO chromatography (10 to 30% EtOAc:heptane)

Sources & evidence

ORD record
ord-4b16701705834caabacd0ca970e00cf2
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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