2,1,3-Benzothiadiazole

Colorless to light brown solid

2.7 Benzo[c][1, 2, 5]thiadiazole (1c) 1, 2-Diaminobenzene (3.250 g, 30.05 mmol) and triethylamine (18 mL, 130.0 mmol) were dissolved in CHExample I-XVPreparation of Compounds 318 and 319General Procedure I-DXA 1000 mL of flask were charged with 1, 2-phenylenediamine (10.0 g, 92.5 mmol), CH2, 1, 3-benzothiadiazole (1) In a similar manner as described in [1], a mixture of o-phenylenediamine (2 g, 18.52 mmol)in 20 mL DCM and triethylamine (10.3 mL, 74.1 mol) were stirred at room temperature untiltotal dissolution of the diamine was observed. Thionyl chloride (2.69 mL, 37.3 mol) wasadded slowly to the reaction mixture via a syringe at 0 °C, the mixture stirred for 30 min atthe same temperature followed by reflux for 5 h. Afterwards, the reaction mixture wasconcentrated under reduced pressure and brought to pH 1 using conc.HCl. The organic layerwas extracted with DCM and then dried over anhydrous Na2SO4. The solvent was evaporatedusing a rotary evaporator under reduced pressure and the residue further purified by columnchromatography using hexane as the eluent. Yield Yield 90percent10.0 g (92.5 mmol) of o-phenylenediamine and 300 ml of dichloromethane were mixed, 37.4 g (370 mmol) of triethylamine was added, stirred and dissolved, 13.6 ml (184.9 mmol) of thionyl chloride was added dropwise, The temperature was refluxed for 5 hours, L cooled to room temperature, concentrated under reduced pressure, add 700ml of water, add concentrated hydrochloric acid to adjust the pH for acid, filter, filter cake and then recrystallized from ethanol, 11g yellow solid, the yield of 88percent.In a two-neck bottle (1000mL), O-phenylenediamine (10.00 g, 92.46 mmol) was dissolved in dichloromethane (400 mL)And a mixed solvent of triethylamine (37.40 g, 370.00 mmol), Thionyl chloride (7.4 mL, 101.70 mmol) was slowly added dropwise.Heated back to reflux for 20 hours.Dichloromethane was removed, petroleum ether (600 mL) was added, filtered, and concentrated.Obtained an off-white powder of benzo[c][1, 2, 5]thiadiazole, That is, product 2 (10.6 g, 84percent).1, 2-Diaminobenzene (10.8g, 0.1mol), thionyl chloride (53mL) are mixed together in a 100-mL flask under rapid stirring. After the mixture is cooled down to 0°C, pyridine (1mL) is added dropwise and refluxed for 24h. Then, the overdose of thionyl chloride is removed under reduced pressure. The residual is poured slowly into distilled water (250mL). The crude product is obtained by steam distillation. After extracting with CHo-phenylenediamine (8.85g, 81.84mmol), 30ml of pyridine and 45ml of chloroform was added to a 500ml three-necked flask, with a pressure-equalizing dropping funnel was slowly added dropwise a solution of 20ml chloroform and thionyl chloride was heated at reflux for 10min, the reaction was stopped, after cooling to room temperature, the reaction solution was poured into a large amount of ice water, CHTo a 500 mL flask, o-phenylenediamine (10.00 g, 92.47 mmol), triethylamine (37.43 g, 369.89 mmol) and 300 mL of anhydrous CHTo a thermometer, Mixing, reflux condenser, Exhaust gas absorption device (800ml saturated NaOH aqueous solution) of the three bottles pass N215min, 100 g of 1, 2-diamine, 374.1 g of triethylamine, Dichloroethane 1200ml, stirring, heating (75 ± 5 ) to complete dissolution, Stop heating(65 ± 3) began to slowly add SOCl2330.6g, Control the rate of dropping so that the system is in a weak return (68 ± 1) ° C state to drip finished, 250min dripping finished; dripping after heating to reflux (72 ± 3) start timing reaction, 2h start every 1h sampling tracking reaction, When the content of raw materials 1, 2-diamine benzene LC 50percent to stop the reaction (see Figure 1, raw materials 1, 2-diamine benzene LC = 0.8465percent, the main peak LC = 52.8365percent);The reaction solution was naturally cooled to room temperature (10 ° C)Add 500ml of water for 10min, Add dilute hydrochloric acid to adjust the PH value to 2 ~ 3, standing 30min, And the aqueous phase was added twice to 200 ml of dichloroethane, Combined organic phase, The organic phase was washed with 2000 ml of water to the neutral phase. The organic phase was dried with 50 g of anhydrous magnesium sulfate for 1 h, Filtered and rinsed with 100 ml of dichloroethane. The filtrate was passed through the column at room temperature (10 ° C)The combined column and eluent were concentrated under reduced pressure (-0.085 MPa, 35 ° C) to no liquid distillate, 102 g of a brown solid was added; 51 ml of ethanol was added and heated to reflux (78 ° C) until complete dissolution, Natural cooling to room temperature (10 ), frozen crystallization 4h, Filtered, and rinsed with ethanol 20ml, Cake cake to constant weight (-0.085Mpa, 25 , 4h) to 77.5g brown crystal is high purity benzo [1, 2, 5] thiadiazole.General procedure: S

Molecular Weight:136.18
XLogP3:2
Hydrogen Bond Acceptor Count:3
Exact Mass:136.00951931
Monoisotopic Mass:136.00951931
Topological Polar Surface Area:54
Heavy Atom Count:9
Complexity:95.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes