Copper-catalyzed three-component synthesis of benzothiazolethiones from o-iodoanilines, isocyanide, and potassium sulfide.

Copper-catalyzed three-component synthesis of benzothiazolethiones from o-iodoanilines, isocyanide, and potassium sulfide.

Organic letters (2014-12-17)

Pan Dang, Weilan Zeng, Yun Liang

ABSTRACT

An efficient copper catalyzed strategy for the synthesis of a variety of benzothiazolethione derivatives has been developed. In the presence of CuCl, the three-component reaction of o-iodoanilines and K2S with p-toluenesulfonylmethyl isocyanide proceeded smoothly to obtain the corresponding benzothiazolethiones in good to excellent isolated yields. Notably, isocyanide functioned as a carbon source and K2S functioned as a sulfur source in this reaction.

MATERIALS

Product Number

Brand

Product Description

05-5870

Sigma-Aldrich

Copper(I) chloride, JIS special grade, ≥95.0%

229628

Sigma-Aldrich

Copper(I) chloride, ≥99.995% trace metals basis

349151

Sigma-Aldrich

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BCR058

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326488

Sigma-Aldrich

Copper, beads, 2-8 mm, ≥99.99% trace metals basis

266744

Sigma-Aldrich

Copper, foil, thickness 1.0 mm, 99.999% trace metals basis

207780

Sigma-Aldrich

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349208

Sigma-Aldrich

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349216

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

349224

Sigma-Aldrich

Copper, wire, diam. 2.0 mm, 99.999% trace metals basis

326410

Sigma-Aldrich

Copper, wire, diam. 0.64 mm, 99.995% trace metals basis

326429

Sigma-Aldrich

Copper, wire, diam. 0.25 mm, 99.999% trace metals basis

GF87182657

Copper, tube, 1000mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%

GF69447280

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GF20661083

Copper, tube, 1000mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%

GF00529040

Copper, sphere, 100pcs, diameter 3.0mm, precision sphere grade 200

GF94832208

Copper, tube, 1000mm, outside diameter 1.0mm, inside diameter 0.24mm, wall thickness 0.38mm, as drawn, 99.9%

GF46821382

Copper, tube, 100mm, outside diameter 1.75mm, inside diameter 0.33mm, wall thickness 0.71mm, as drawn, 99.9%

GF56401523

Copper, rod, 500mm, diameter 4.8mm, hard, 99.9%

GF16694006

Copper, rod, 50mm, diameter 6.35mm, as drawn, 99.999%

GF60058346

Copper, sphere, 1000pcs, diameter 3.0mm, precision sphere grade 200

GF77355579

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GF23864463

Copper, tube, 1000mm, outside diameter 0.75mm, inside diameter 0.23mm, wall thickness 0.26mm, as drawn, 99.9%

GF53474980

Copper, tube, 100mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%

GF37804901

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Copper, sphere, 200pcs, diameter 3.0mm, precision sphere grade 200

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