2-Amino-5,6-dichlorobenzothiazole

White powder

5,6-dichloro-2-benzothiazolamine appears as white solid or powder. (NTP, 1992)

5,6-dichloro-2-benzothiazolamine appears as white solid or powder. (NTP, 1992)

To a mixture of 3, 4-dichloroaniline (10 g, 62 mmol) and potassium thiocyanate (48 g, 0.49 mol) in acetic acid (160 mL) at 0 °C was added slowly with constant stirring a solution of liquidbromine (31 g, 0.19 mol) in acetic acid (160 mL). The temperature was maintained at 0 °C throughout the addition. The solution was stirred for 2 hours at 0°C and 14 hours at 15 °C, then diluted with water (100 mL), adjusted to pH 78 with ammonium hydroxide and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (3 x 300 mL) and concentrated in vacuo. The residue was purified by prep-HPLC [Instmment: GX-B; Column: GEMNI 250 x 50 mm, particle size: 10 .im; Mobile phase: 25-50percent acetonitrile in H20 (add 0.1percent TFA, v/v)j to give compound B- 24 (2.6 g, 19percent yield) as a white solid. LCMS (J): tR=0.694 mi (ES) m/z (M+H)219.0. ‘H-NMR (CD3OD, 400 MHz): 7.89 (s, 1H), 7.55 (s, 1H).j00320j To a mixture of 3, 4-dichloroaniline (10 g, 62 mmol) and potassium thiocyanate (48 g, 0.49 mol) in acetic acid (160 mL) at 0 °C was added slowly with constant stirring a solution of liquidbromine (31 g, 0.19 mol) in acetic acid (160 mL). The temperature was maintained at 0 °C throughout the addition. The solution was stirred for 2 hours at 0°C and 14 hours at 15 °C, then diluted with water (100 mL), adjusted to pH 78 with ammonium hydroxide and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (3 x 300 mL) and concentrated in vacuo. The residue was purified by prep-HPLC [Instmment: GX-B; Column: GEMNI 250 x 50 mm, particle size: 10 .im; Mobile phase: 25-50percent acetonitrile in H20 (add 0.1percent TFA, v/v)j to give compound B- 24 (2.6 g, 19percent yield) as a white solid. LCMS (J): tR=0.694 mi (ES) m/z (M+H)219.0. ‘H-NMR (CD3OD, 400 MHz): 7.89 (s, 1H), 7.55 (s, 1H).Listed below are some typical examples of said 2-aminobenzothiazole compounds:...2-amino-6-thiocyanobenzothiazole2-amino-6-methylbenzothiazole2-amino-4, 6-dichlorobenzothiazole2-amino-4, 6-dibromobenzothiazolej00322j To a solution of compound B-24 (0.25 g, 1.1 mmol), tert-butyl nitrite (0.35 g, 3.4 mmol), p-toluenesulfonic acid monohydrate (0.59 g, 3.4 mmol) and tetrabutylammonium bromide (2.2 g, 6.8 mmol) in acetonitrile (25 mL) was added copper(I) bromide (16 mg, 0.11 mmol). The reaction mixture was stirred at 30 °C for 4 hours, and then concentrated. The residue was purified by column chramotagraphy [petroleum ether: ethyl acetate = 20:1) to give compound B-25 (0.18 g, 56percent yield) as a yellow solid.1.09 g (0.005 mol)(1) in 250ml 4-neck flask was added N- -N- cyanoethyl hydroxyethyl toluidine 49g, triethyl benzyl ammonium chloride 2.2g, acrylonitrile, 17g, was stirred at 10-15 , and 30percent caustic solution of 12.5g, after completion of the addition stirring until completion of the reaction, acetic acid was added and set aside.(2) 500ml 4-neck flask was added sulfuric acid 150g, 2- amino-5, 6-thiazol-dichlorobenzene and 50g, 60 stirring until dissolved, adding sodium sulfate nitroxyl 80g, water 120g, cooling to 10 , slowly diazonium sulfate was added 80g, completion of the dropwise addition, the reaction at 0-5 about 2 hours to complete the reaction to obtain a diazo solution.(3) adding water 3000ml beaker 100g, 350 g of ice, the step (1) of the intermediate prepared, stir, was added slowly below 0 step (2) the obtained diazo solution was stirred until the reaction was complete, filtered, washed with water , and dried to obtain 100g compound of formula (I-1).In beating the pot by adding 28percent (mass percent concentration of the solvent is sulfuric acid, the same below) nitriteSulfuric acid 700kg, stirring slowly open 2-amino-5, 6-chlorobenzothiazole 1100kg, cast BiIncubated at 30-40 for one hour to obtain a homogeneous mixture, still stand;Add 45percent (mass percent concentration, the same below) in sulfuric acid solution 3000kg diazo kettle, Turn down to below freezing brine stirred -2 , slowly into the above mixture, the addition was completed, at -5 Less heat to complete the reaction, spare;Coupling was added into the kettle bottom water 6000kg, 98percent sulfuric acid 800kg, then add AEO-9 Emulsifier10kg and N, N- diethylaniline-diacetoxy 300kg, beating 20min, administration ice cooling, a solution ofAbove diazo solution, plus complete 0 ~ 5 for 3 hours, after passing the end point detection, start adding ammonia waterSolution (mass percent concentration of 10percent) adjusting the pH value to 6.0 to 7.0, and then heatedTo 80 ~ 85 , stirring revolutions Jing 1 hour until the dye transfer backward filter crystal filter press, washed with water to neutral, To give 153: 1 red disperse dye cake, prepared after the mother liquor collected water for ammonium sulfate, 153: 1Red disperse dye of the formula in the following components

Used as disperse dye and azo dye intermediate

Molecular Weight:219.09
XLogP3:3.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:217.9472247
Monoisotopic Mass:217.9472247
Topological Polar Surface Area:67.2
Heavy Atom Count:12
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes