Preparation method of oxalylsulfonyl hydrazide and its application in sulfonylation reaction of olefins
A technology of oxalylsulfonyl hydrazide and chemical reaction, applied in the field of organic chemical synthesis, can solve problems such as no reports on the preparation of oxalylsulfonyl hydrazide, and achieve the effects of cheap raw materials, simple process and easy preparation
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Embodiment 1
[0021] Embodiment one (preparation of oxalyl p-toluenesulfonyl hydrazide):
[0022]
[0023] In a 100ml reaction flask, add 50ml of solvent methylene chloride and 3.2 grams (25mmol) of oxalyl chloride successively, cool in an ice bath to zero degree, then add 9.3 grams (50mmol) of p-toluenesulfonyl hydrazide and 5 grams (50mmol) of triethylamine successively dropwise. ), each dropping time was 10 minutes. After the dropwise addition, the reaction was continued at zero temperature for 5 hours, extracted three times with water and ethyl acetate. The water layer was removed, and the organic layer was dried with anhydrous sodium sulfate. The solvent was removed with a rotary evaporator, and then it was purified by silica gel chromatography (methanol / dichloromethane=1 / 10) to obtain 8.8 grams of pure oxalyl-p-toluenesulfonyl hydrazide, with a yield of 82%.
Embodiment 2
[0025] Add 2ml of solvent ethanol, 0.26g (0.6mmol) of oxalyl-p-toluenesulfonyl hydrazide, 0.052g (0.5mmol) of styrene, and 1.9mg (0.01mmol) of catalyst cuprous iodide in a 10ml reaction tube, open the Reaction at room temperature. Track the reaction until the complete disappearance of oxalyl-p-toluenesulfonyl hydrazide. After the reaction, it was extracted three times with water and ethyl acetate. The aqueous layer was removed, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed by a rotary evaporator, and then purified by silica gel chromatography (ethyl acetate / petroleum ether=1 / 10) to obtain 0.114 g of pure 2-p-toluenesulfonylacetophenone with a yield of 84%. 1 H NMR (400MHz, CDCl 3 )δ7.97(d, J=7.7Hz, 2H), 7.78(d, J=8.1Hz, 2H), 7.64(t, J=7.3Hz, 1H), 7.50(t, J=7.6Hz, 2H) ,7.35(d,J=8.0Hz,2H),4.74(s,2H),2.46(s,3H). 13 C NMR (101MHz, CDCl 3 ) δ 188.15, 145.36, 135.82, 134.31, 129.84, 129.34, 128.84, 128.62, 63.61, 21.70.
Embodiment 3
[0027] In Reaction Example 2, except that 0.052 g (0.5 mmol) of styrene was changed to 0.092 g (0.5 mmol) of 1-bromo-4-vinylbenzene, the reaction was carried out in the same manner as in Example 2. 2-p-toluenesulfonyl-4'-bromoacetophenone, yield 85%. 1 HNMR (400MHz, CDCl 3 )δ8.02(t, J=1.8Hz, 1H), 7.91(ddd, J=7.8, 1.6, 1.0Hz, 1H), 7.80–7.71(m, 3H), 7.38(dd, J=15.3, 7.8Hz ,3H),4.70(s,2H),2.47(s,3H). 13 C NMR (101MHz, CDCl 3 ) δ 186.69, 144.92, 137.41, 132.04, 130.34, 128.55, 127.98, 123.18, 63.98.
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