High-efficiency preparation method for sulfoxide sulfinyl urea compounds
A sulfoxide sulfinyl urea and compound technology, which is applied in the field of high-efficiency preparation of sulfoxide sulfinyl urea series compounds, can solve the problems of unstable chemical properties of isocyanates, highly toxic properties, easy hydrolysis and deterioration, and the like. It is beneficial to separation and purification, good reactivity and good application prospect.
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Example Embodiment
[0014] Example one:
[0015]
[0016] Under air atmosphere, dissolve 4-methoxybenzoyl azide (63.7mg, 0.36mmol) in organic solvent acetonitrile (1mL), add dropwise to diphenylsulfinimide in a magnetic stirrer at 80℃ (65.1 mg, 0.3 mmol) in acetonitrile (1 mL) solution, the reaction was continued for 3 hours under an air atmosphere, and the reaction process was monitored with a TLC panel until the reaction was complete. After treatment, the pure product 1-sulfinyl-3-phenylurea compound 3a was separated by flash column chromatography. Yield: 96%. The following are the NMR experimental data of product 3a:
[0017] 1 H NMR(400MHz,d6-DMSO)δ9.50(s,1H), 8.03(d,J=6.8Hz,4H), 7.63(d,J=7.7Hz,6H), 7.42(d,J=8.6Hz ,2H), 6.81(d,J=8.2Hz,2H), 3.68(s,3H).
[0018] 13 C NMR (100MHz, d6-DMSO) δ 157.3, 154.8, 140.6, 133.8, 130.2, 127.9, 120.4, 120.0, 114.2, 55.6.
Example Embodiment
[0019] Embodiment two:
[0020]
[0021] Under air atmosphere, 4-methylbenzoyl azide (58mg, 0.36mmol) was dissolved in organic solvent acetonitrile (1mL) and added dropwise to diphenylsulfinimide (65.1) in a magnetic stirrer at 80℃. mg, 0.3 mmol) in acetonitrile (1 mL) solution, the reaction was continued for 3 hours under air atmosphere, and the reaction process was monitored with a TLC panel until the reaction was complete. After treatment, the pure product 1-sulfinyl-3-phenylurea compound 3b was separated by flash column chromatography. Yield: 91%. The following are the NMR experimental data of product 3b:
[0022] 1 H NMR(400MHz,d6-DMSO)δ9.55(s,1H), 8.03(d,J=7.1Hz,4H),7.71-7.59(m,6H),7.39(d,J=8.3Hz,2H) ,7.02(d,J=8.1Hz,2H),2.21(s,3H).
[0023] 13 C NMR (100MHz, d6-DMSO) δ 157.3, 140.5, 138.2, 133.8, 131.1, 130.2, 129.4, 128.0, 118.6, 20.8.
Example Embodiment
[0024] Embodiment three:
[0025]
[0026] Under air atmosphere, dissolve benzoyl azide (882mg, 6mmol) in organic solvent acetonitrile (10mL), and add dropwise to diphenylsulfinimide (1.085g, 5mmol) at 80℃ in a magnetic stirrer. In the acetonitrile (10 mL) solution, the reaction was continued for 3 hours under an air atmosphere. During the reaction, the reaction was monitored with a TLC panel until the reaction was complete. After treatment, the pure product 1-sulfinyl-3-phenylurea compound 3c was separated by flash column chromatography, and the yield was 87%. The following are the NMR experimental data of product 3c:
[0027] 1 H NMR(400MHz,d6-DMSO)δ9.65(s,1H), 8.04(d,J=7.2Hz,4H), 7.69-7.62(m,6H), 7.52(d,J=8.0Hz,2H) ,7.22(t,J=7.7Hz,2H),6.93(t,J=7.2Hz,1H).
[0028] 13 C NMR (100MHz, d6-DMSO) δ 157.4, 140.7, 140.5, 133.9, 130.2, 129.0, 128.0, 122.3, 118.6.
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