Related Products of 63624-28-2,Some common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, molecular formula is C8H9ClO4S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
301 mg of the compound obtained in step 16-2 (diastereoisomer mixture) was added under ice cooling and a nitrogen atmosphere to a 3 mL tetrahydrofuran solution of 26 mg of sodium hydride, and the reaction mixture was stirred for 20 minutes. After this, a 2 mL tetrahydrofuran solution of 170 mg of 2,4-dimethoxybenzenesulfonyl chloride was added dropwise, and the reaction mixture was stirred for 2 hours at room temperature. Then 5mL of ethylacetate and 10mL of a 5% potassium carbonate aqueous solution were added and the reaction mixture was stirred for 30 minutes at room temperature. After liquid separation, the aqueous layer was extracted with ethyl acetate (10 mL × 3), and the combined organic layer was dried with sodium sulfate, after which the drying agent was filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was separated and purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/acetone = 99/1; v/v) to obtain two kinds of diastereoisomer of the titled compound in amounts of 115 mg (isomer A: colorless, amorphous) and 127 mg (isomer B: colorless, amorphous). Isomer A: [alpha]D25 = -248 (c = 0.183, chloroform) MS (ESI pos.) m/z : 680([M+H]+), (ESI pos.) m/z : 702([M+Na]+ 1H-NMR (499 MHz, CDCl3) delta (ppm) ; 1.89 (s, 1 H), 2.19 – 3.94 (m, 21 H), 4.65 – 5.06 (m, 1 H), 5.23 – 5.44 (m, 1 H), 6.43 (s, 1 H), 6.57 (dd, J =9.0, 2.3 Hz, 2 H), 6.97 – 7.05 (m, 1 H), 7.42 (d, J=8.8 Hz, 1 H), 7.75 (s, 1 H), 7.93 (d, J=8.5 Hz, 1 H), 8.09 – 8.20 (m, 1 H) Isomer B: [alpha]D25 = +211 (c = 0.200, chloroform) MS (ESI pos.) m/z : 680([M+H]+), (ESI pos.) m/z : 702([M+Na]+) 1 H-NMR (499 MHz, CDCl3) delta (ppm) ; 1.88 – 2.23 (m, 2 H), 2.33 (s, 3 H), 2.55 – 2.81 (m, 6 H), 3.36 (s, 3 H), 3.47 – 3.63 (m, 1 H), 3.79 – 3.88 (m, 7 H), 4.07 – 4.19 (m, 1 H), 4.95 – 5.19 (m, 1 H), 6.48 (d, J=2.1 Hz, 1 H), 6.57 (dd, J=8.8, 2.1 Hz, 1 H), 6.63 (d, J=8.2 Hz, 1 H), 6.99 – 7.07 (m, 1 H), 7.41 – 7.48 (m, 1 H), 7.67 (s, 1 H), 7.92 – 8.01 (m, 1 H), 8.13 (d, J=8.8 Hz, 1 H)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dimethoxybenzene-1-sulfonyl chloride, its application will become more common.
Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1659121; (2006); A1;,
Chloride – Wikipedia,
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