In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 37441-50-2,1,2-Thiazinane 1,1-dioxide, as follows.37441-50-2
Step2 A strong glass tube was charged with Pd2(dba)3 (6.4 mg; 0.007 mmol), xantphos (12 mg; 0.02 mmol), 1,2-thiazinane-1,1-dioxide (115 mg; 0.85 mmol), and Cs2CO3 (323 mg; 0.99 mmol).The tube was capped with a rubber septum, evacuated and backfilled with nitrogen. 6-Bromo-1-methyl-1H-indole carboxylic acid ethyl ester (200 mg; 0.71 mmol) in 1 ml of 1,4-dioxane was added through the septum.The septum was replaced with a Teflon screwcap.The tube was sealed, and the mixture was stirred at 100 C. for 64 hours.The reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 ml), filtered, and concentrated in vacuo.The crude material was purified by flash chromatography (silica gel, ethyl acetate-hexane 1:1) to afford 190 mg (66%; m/z 337) of colorless crystals.This compound was dissolved in a mixture of tetrahydrofuran (4 ml), methanol (2 ml) and water (1 ml).To this solution was added dropwise LiOH monohydrate (95 mg; 2.26 mmol) dissolved in 1 ml water and the mixture was stirred at room temperature for 16 h.The reaction mixture was partition between ethyl acetate and water.The aqueous layer was acidified with 2N HCl to ph ~3-4 and extracted with ethyl acetate.The organic layer was washed with brine and dried (Na2SO4) and evaporated in vacuo.Yield 131 mg of 6-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)-1-methyl-1H-indole-2-carboxylic acid as a white powder (75%); m/z 307., 37441-50-2
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Thiazinane 1,1-dioxide, and friends who are interested can also refer to it.
Reference£º
Patent; Bamberg, Joe Timothy; Gabriel, Tobias; Krauss, Nancy Elisabeth; Mirzadegan, Taraneh; Palmer, Wylie Solang; Smith, David Bernard; US2004/77646; (2004); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem