2-IODOBENZOTHIAZOLE synthesis

5synthesis methods

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

95-16-9

1123-99-5

The general procedure for the synthesis of 2-iodobenzothiazole from benzothiazole was as follows: benzothiazole (1 mmol, 135.9 mg) and perfluorobutyl iodide (1.1 mmol, 380.5 mg) were placed in a 10 mL round bottom flask. 5 mL of N,N-dimethylformamide and sodium tert-butoxide (0.5 mmol, 48.1 mg) were added. The reaction mixture was stirred at room temperature for 20 min and the progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was poured into water and extracted with dichloromethane. The organic phase was collected and dried with anhydrous sodium sulfate, followed by removal of dichloromethane by rotary evaporator to give the crude product. The crude product was purified by silica gel column chromatography using petroleum ether and ethyl acetate (v/v=30:1) as eluents to give 2-iodobenzothiazole (white solid, 257.6 mg, 99% yield). In addition, the crude product can also be purified by recrystallization: the crude product was first washed with cold water, filtered, and dissolved in ethanol (2 mL). After heating until complete dissolution, it was left to stand and slowly cooled to induce precipitation of crystals.

136-95-8 Synthesis

136-95-8
411 suppliers
$7.00/25g

1123-99-5
117 suppliers
$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

95-16-9
437 suppliers
$14.14/10gm:

1123-99-5
117 suppliers
$19.00/250mg

References

615-20-3 Synthesis