ChemicalBook CAS DataBase List 2-IODOBENZOTHIAZOLE

2-IODOBENZOTHIAZOLE synthesis

5synthesis methods

Product Name:2-IODOBENZOTHIAZOLE
CAS Number:1123-99-5
Molecular formula:C7H4INS
Molecular Weight:261.08

136-95-8 Synthesis

136-95-8
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$7.00/25g

1123-99-5
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$19.00/250mg

Yield: 84.7%

Reaction Conditions:

with toluene-4-sulfonic acid;potassium iodide;sodium nitrite in water;acetonitrile at 0 - 20;

Steps:

2-iodobenzo[d]thiazole (7)
To a solution of 2-aminobenzothiazole (6) (3.75g, 25mol) and p-TsOH (15g, 75mmol) in acetonitrile (100ml) was added a mixture solution of KI (10.5g, 65mmol) and NaNO₂ (3.5g, 50mol) in water (15ml) at 0°C. The reaction solution was stirred at 0°C for 2h, and then at RTovernight. To the reaction solution was added around 350ml of water, adjust the solution pH to 8-9 with NaHCO₃ and added Na₂S₂O₃, filtered and the solid was washed to give brown solid 5.52g (yield 84.7%). TLC: Rf: 0.6 (hexane/ethyl acetate=6/1). MS (ESI) m/z 262 (M⁺+H);¹HNMR (CDCl₃, 300MHz) δ 8.06 (1H, dd, J1=7.5Hz, J2=1.8Hz), 7.87 (1H, dd, J1=6.9Hz,J2=1.5Hz), 7.50~7.38 (2H, m).

References:

Qi, Jianjun;Tung, Ching-Hsuan [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 1,p. 320 - 323] Location in patent:supporting information; experimental part

95-16-9 Synthesis