Method for generating sulfenamide compounds with s-n bonds by catalyzing molecular oxygen oxidation in aqueous phase
A technology for sulfenamides and compounds, which is applied in the field of organic sulfur-sulfur bond synthesis, can solve the problems of increasing the difficulty and steps of post-treatment and purification of products, and difficult to avoid salt-containing wastewater, etc., and achieves strong industrial application prospects, environmental friendliness, and side effects. The effect of less product
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Embodiment 1
[0028] Synthesis of sulfenamide compounds containing sulfur-nitrogen bonds in an oxygen atmosphere:
[0029] In a 250 mL reactor, 8 g of 2-mercaptobenzothiazole, 15 g of thiazine, 0.16 g (2 wt%) of tetracarboxymanganese phthalocyanine tetrasodium [MnPc(COONa) 4 ], 0.08 g (1 wt%) nickel tetrasodium tetracarboxyphthalocyanine [NiPc(COONa) 4 ], and 120 mL of water; heated to 90 °C under stirring, and oxygen was introduced to keep the pressure in the reactor at 1.0 MPa. After 18 hours of reaction, the reaction was stopped, cooled, filtered, washed with 100 mL of water, and dried to obtain white The solid was 7.2 g. The structure of the product was determined to be 2-thiazinthiobenzothiazole by NMR, MS and other methods. The yield was 78%. The purity of the product analyzed by liquid chromatography was 99%.
Embodiment 2
[0031] Synthesis of sulfenamide compounds containing sulfur-nitrogen bonds in air atmosphere:
[0032] In a 100 mL reactor, put 3 g of 2-mercaptopyridine, 6 g of cyclohexylamine, and 4 mg of cobalt tetrasulfonate phthalocyanine [CoPc(SO 3 h) 4 ], 3 mg copper tetracarboxyphthalocyanine [CuPc(COOH) 4 ], 2 mg cesium tetrasulfonate phthalocyanine [CePc(SO 3 h) 4 ] and 60 mL of water; heated to 80°C with stirring, and air was injected to keep the pressure in the reactor at 1.0 MPa. After 2 hours of reaction, the reaction was stopped, cooled, filtered, washed with 30 mL of water, and dried to obtain 5.4 g of the product N -cyclohexyl-pyridine-base sulfenamide, the yield is 96%, and the purity of the product analyzed by liquid chromatography is 99%.
Embodiment 3
[0034] Synthesis of sulfenamide compounds containing sulfur-nitrogen bonds in an oxygen-enriched air atmosphere:
[0035] In a 250 mL reactor, put 30 g of 2-mercaptobenzothiazole, 30 g of n-butylamine, and 3 mg of tetrapotassium tetrasulfonic acid phthalocyanine tungsten [WPc(SO 3 K) 4 ] and 90 mL of water; heat up to 65°C under stirring, press in oxygen-enriched air [oxygen:air (wt:wt) = 1:2], keep the pressure in the reactor at 0.05 MPa, stop the reaction after 8 hours of reaction, Cool, filter, wash with water, and dry to obtain 29.1 g of product N -n-butyl-2-benzothiazole sulfenamide, the yield is 78%, and the liquid chromatography analysis product purity is 96%.
[0036]The organic matter containing sulfur-nitrogen bond was synthesized by the same method as in Example 1, and its various reaction conditions and reaction results are shown in Table 1.
[0037] Table 1 Synthesis of various organic compounds containing sulfur-nitrogen bonds under different conditions
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