2-Amino-6-benzothiazolecarboxylic acid

Light brown powder

Synthesis of 2-aminobenzothiazole-6-carbolic Acid(2)NaSCN (65 g, 0.8 mol) was added to a suspension of commercially available 4-amino-benzoic acid (1, 100 g, 0.73 mol) in MeOH followed by the addition of Br(2) 2-amino-benzo[d]thiazole-6-carboxylic and:; 13.0g (0.07mol) 4-amino-3-thiocyano-benzonitrile was weighed, dissolved in 120ml water, stirred uniformly, added with 60ml concentrated hydrochloric acid, reacted under refluxing and stirring at about 100°C for 6h. After the reaction, the reaction mixture was stood, filtered to obtain a precipitated solid, and dried out to obtain a light yellow solid product 8.5g (59.0percent). mp 280-282°C. (2)(2) 2-amino-benzo[d]thiazole-6-carboxylic and:; 13.0g (0.07mol) 4-amino-3-thiocyano-benzonitrile was weighed, dissolved in 120ml water, stirred uniformly, added with 60ml concentrated hydrochloric acid, reacted under refluxing and stirring at about 100°C for 6h. After the reaction, the reaction mixture was stood, filtered to obtain a precipitated solid, and dried out to obtain a light yellow solid product 8.5g (59.0percent). mp 280-282°C. (2)Weigh 13.0 g (0.07 mol) of 4-amino-3-thiocyano-benzonitrile, Dissolve in 120ml water, stir evenly, add 60ml concentrated hydrochloric acid, The reaction was stirred under reflux at about 100 ° C for 6 h. After the reaction was completed, it was allowed to stand.The solid was separated by filtration and dried to give 8.5 g (59.0percent).Synthesis of 2-aminobenzothiazole-6-carbolic Acid(2)NaSCN (65 g, 0.8 mol) was added to a suspension of commercially available 4-amino-benzoic acid (1, 100 g, 0.73 mol) in MeOH followed by the addition of BrPreparation of 2-amino-3-methyl-6-carboxybenzothiazolium iodide As shown in FIG. 3, 2-amino-3-methyl-6-carboxybenzothiazolium iodide, 3, is produced from compound 2 above. Thirty four grams of To a solution of Benzyl bromide (129 mI_, 1 .08 mmol) was added dropwise to a solution of 2-amino-benzothiazole-6- carboxylic acid (200 mg, 1 .03 mmol) in acetonitrile (10 ml_) and the mixture was stirred at r.t. for 18h. The reaction mixture was diluted with water and stirred for 15 mins. The yellow precipitate was filtered, washed (water) and triturated in minimal Et20. After drying under vacuum the title compound was isolated as a yellow solid (178 mg, 61 %). NMR dH(500 MHz, DMSO-d6) 8.34 (t, J = 7.7 Hz, 1 H), 7.93 (s, 2H), 7.88 - 7.81 (m, 1 H), 7.54 - 7.46 (m, 2H), 7.45 - 7.32 (m, 4H), 5.33 (s, 2H).LCMS (Method C): 2.99 min (285.2, MH+).

Molecular Weight:194.21
XLogP3:1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:194.01499861
Monoisotopic Mass:194.01499861
Topological Polar Surface Area:104
Heavy Atom Count:13
Complexity:224
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes