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Stage #1: With copper(l) iodide; sodiumsulfide nonahydrate In N,N-dimethyl-formamide at 80℃; Inert atmosphere Stage #2: With acetic acid In N,N-dimethyl-formamide at 130℃; for 36 h; Inert atmosphere
General procedure: A Schlenk tube was charged with ethyl 2-iodo-phenylcarbamates (1 mmol), CuI (19mg, 0.1 mmol), and Na2S*9H2O (3 mmol). The tube was evacuated and backfilled with argon (3 times), and the 2 mL of DMF was added. The reaction mixture wasstirred at 80 °C for 10-16 h, then 3 mL of AcOH was added to the cooled reaction mixture and the mixture was stirred at 130 °C for another 36 h. Saturated NaHCO3 (10mL) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with H2O, brine, and dried over Na2SO4. After removal of the solvent in vacuo, the residue was purified by column chromatography on silica gel to provide the desired benzothiazolone.
3-acetyl-5-methoxy-2(3H)-benzothiazolone[ No CAS ]
[ 40449-35-2 ]
[ 107-06-2 ]
[ 15193-51-8 ]
Yield
Reaction Conditions
Operation in experiment
With hydrogenchloride; In ethanol; water; pyrographite;
(b) 5-Methoxy-2(3H)-benzothiazolone 7.0 gm (0.0314 mol) of 3-acetyl-5-methoxy-2(3H)-benzothiazolone were suspended in a mixture of 210 ml of 5 N hydrochloric acid and 70 ml of ethanol, and the suspension was refluxed for one hour. The still hot mixture was filtered, diluted with 200 ml of water and brought to a temperature of 5 C. by external cooling with ice. After standing for 2 hours, the precipitate was filtered off, and the dried product was purified chromatographically on silica gel, using 1,2-dichloroethane-acetone (volume ratio 9:1) for elution, and finally recrystallized from methanol and from 1,2-dichloro-ethane, each time in the presence of activated charcoal. The slightly yellow crystals obtained with a yield of 3.25 gm (57% of theory) melted at 168-170 C. C8 H7 NO2 S (181.21)-- Calc.: C-53.03%; H-3.89%; N-7.73%; S-17.69%. Found: C-53.20%; H-3.90%; N-7.74%; S-17.70%.
General procedure: A Schlenk tube was charged with ethyl 2-iodo-phenylcarbamates (1 mmol), CuI (19mg, 0.1 mmol), and Na2S*9H2O (3 mmol). The tube was evacuated and backfilled with argon (3 times), and the 2 mL of DMF was added. The reaction mixture wasstirred at 80 C for 10-16 h, then 3 mL of AcOH was added to the cooled reaction mixture and the mixture was stirred at 130 C for another 36 h. Saturated NaHCO3 (10mL) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with H2O, brine, and dried over Na2SO4. After removal of the solvent in vacuo, the residue was purified by column chromatography on silica gel to provide the desired benzothiazolone.
5-methoxy-6-nitro-1,3-benzothiazol-2(3H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84%
With nitric acid; In sulfuric acid; at 12℃; for 0.5h;
A solution of 6.00 g (33.1 mmol) <strong>[15193-51-8]5-methoxy-1,3-benzothiazol-2(3H)-one</strong> (CAS-No15193-51 -8) in 80 mL sulfuric acid was cooled to -12C. A mixture comprising 5.01 mL nitric acid (40%) and 4.80 mL sulfuric acid was added slowly. After 30 minutes the mixture was poured into ice-water. The precipitate was filtered, washed with water and hexane and dried to give 6.30 g (84%) of the title compound.
benzyl2-(5-methoxy-2-oxobenzo[d]thiazol-3(2H)-yl)acetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
General procedure: A mixture of appropriate amine 74a-i (1 equiv), 78 K2CO3 (1.05 equiv), and a catalytic amount of NaI in 79 acetone was stirred at room temperature. Benzyl, ethyl, or 80 methyl bromoacetate 75, 76, 77 (1.1 equiv) was added dropwise to the mixture, which was then refluxed for 2h (Scheme 2, see also Supplementary data).
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