3-OXO-2,3-DIHYDRO-1,2-BENZISOTHIAZOLE-6-CARBOXYLIC ACID 1,1-DIOXIDE synthesis
- Product Name:3-OXO-2,3-DIHYDRO-1,2-BENZISOTHIAZOLE-6-CARBOXYLIC ACID 1,1-DIOXIDE
- CAS Number:90779-46-7
- Molecular formula:C8H5NO5S
- Molecular Weight:227.19
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Yield: 73.63% ， 24.76%
Reaction Conditions:
with sodium hypochlorite;dichloro(2,2'-bipyridine)nickel(II) at 25 - 40; for 4.25 h;Overall yield = 75.53 %; Overall yield = 19.99 g;
Steps:
1.2 Step 2: Preparation of 2-sulfamoyl-terephthalic acid (Compound (III))
40 ml (10.8 mmol) of Ni(BiPy)Cl2 solution and 127 ml (21.6 mmol) of sodium hypochlorite were charged in a round bottom flask. The mixture was stirred at 25-30°C for 30 minutes until black precipitates were formed. 20 gr (108 mmol) of 2,5-Dimethyl-benzenesulfonamide (Compound II) was added at 25-30°C and the reaction mixture was stirred for 15 min. 507 ml (1.08 moles) of 127 gr/L Sodium hypochlorite solution was added dropwise at 35-40°C and the reaction was stirred for 4 hours.The reaction progress was monitored by HPLC until 2,5-dimethyl-benzenesulfonamide (Compound II) was present at a concentration of less than 1%. 80 ml of 38% HCl was added dropwise until pH is highly acidic (pH = 1-2) and gas evolution was observed. After which, 80 gr (420.8 mmol) of sodium metabisulfite was added in portions at 20-50°C until no colorization on starch iodide paper was observed. The reaction mass was cooled to 25-30°C and stirred for 1 hour at 25°C. The solid formed was filtered, washed with 20 ml water at room temperature and dried in vacuum at 55-60°C. Yield: 19.99 gr (75.53%). Two major products, were observed namely 2-sulfamoyal terephthalic acid (formula III) (73.63%) and 1,1,3-trioxo-1,2-benzothiazole-6-carboxylic acid (formula VII) (24.76%).
References:
ADAMA AGAN LTD.;PILLAI, Bijukumar, Gopinathan;MIRILASHVILI, Sima;BARDA, Yaniv;HAMIRANI, Bhavinkumar, P.;MEKA, Bhoopal;MANNAM, Sreedevi WO2017/115137, 2017, A1 Location in patent:Page/Page column 21; 22
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$33.39/250mg
90779-46-7
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19040-62-1
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90779-46-7
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