ChemicalBook CAS DataBase List 1-(PHENYLSULFONYL)-1H-BENZOTRIAZOLE

1-(PHENYLSULFONYL)-1H-BENZOTRIAZOLE synthesis

8synthesis methods

Product Name:1-(PHENYLSULFONYL)-1H-BENZOTRIAZOLE
CAS Number:4106-18-7
Molecular formula:C12H9N3O2S
Molecular Weight:259.28

95-14-7 Synthesis

95-14-7
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$6.00/100g

873-55-2 Synthesis

873-55-2
385 suppliers
$10.00/5g

4106-18-7
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$264.00/1g

Yield:4106-18-7 97%

Reaction Conditions:

with iodine in water;ethyl acetate at 20; for 3 h;Mechanism;Reagent/catalyst;Solvent;Time;

Steps:

A typical procedure for the catalytic N-sulfonylation of benzotriazoles using I₂ as catalyst includes: in EtOAc-H₂O (10:1) mixture solvent (2 mL), benzotriazole 1a (0.3 mmol), sodium benzenesulfinate 2a (0.9 mmol), I₂ (0.06 mmol) were added successively.
The suspension mixture was vigorously stirred at room temperature for 3 h.
Upon completion, the reaction was quenched by addition of sat. aq. Na₂S₂O₃ (2 mL), basified with sat. aq. Na₂CO₃ (8 mL) and H₂O (5 mL).
The mixture was extracted with CH₂Cl₂ (3* 5 mL) and the combined organic phase was dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure.
The residue was then purified by TLC technique (petroleum ether/ethyl acetate = 3:1, v/v) to furnish 1-phenylsulfonylbenzotriazole 3a
[28]
in 97% yield.
Compound 3a: Pale yellow solid; mp 122-123 °C; ¹H NMR (500 MHz, CDCl₃): δ 8.15-8.11 (m, 3H), 8.09 (d, 1H, J = 8.4 Hz), 7.70-7.64 (m, 2H), 7.57-7.53 (m, 2H), 7.52-7.47 (m, 1H); ¹³C NMR (125 MHz, CDCl₃): δ 145.4, 137.0, 135.2, 131.6, 130.3, 129.6, 127.8, 125.9, 120.5, 111.9; IR (film, cm^-1): ν 3094, 3069, 1586, 1480, 1386, 1194, 955, 726, 589; MS (EI, m/z, %): 260 (M + 1, 100).