| Identification | More | [Name]
2-Aminobenzothiazole-6-carboxylic acid | [CAS]
93-85-6 | [Synonyms]
2-AMINO-1,3-BENZOTHIAZOLE-6-CARBOXYLIC ACID
2-AMINO-6-BENZOTHIAZOLECARBOXYLIC ACID
2-AMINO-BENZOTHIAZOLE-6-CARBOXYLIC ACID
6-BENZOTHIAZOLECARBOXYLIC ACID, 2-AMINO-
AKOS BB-7723
AKOS BBS-00000327
ASISCHEM B67429
SALOR-INT L481106-1EA
2-Aminobenzothiazolepurum
forgravimetricdetermination(ofHg)
forspectrophotometricdet.(ofPd)
6-Benzothiazolecarboxylicacid,2-amino-(6CI,8CI,9CI)
2-aminobenzo[d]thiazole-6-carboxylic acid | [EINECS(EC#)]
202-283-8 | [Molecular Formula]
C8H6N2O2S | [MDL Number]
MFCD00054180 | [Molecular Weight]
194.21 | [MOL File]
93-85-6.mol |
| Hazard Information | Back Directory | [Chemical Properties]
Light brown powder | [Antimicrobial activity]
2-Aminobenzothiazole-6-carboxylic acid is a synthetic antibacterial agent that inhibits bacterial growth by binding to the enzyme urokinase-type plasminogen (uPA) and preventing it from converting plasminogen to plasmin. This drug has been shown to have inhibitory properties against a wide range of bacteria, including Staphylococcus and Escherichia coli. | [Synthesis]
Steps for the synthesis of 2-aminobenzothiazole-6-carboxylic acid: (2) Sodium thiocyanate (NaSCN, 65 g, 0.8 mol) was added to a methanol (MeOH) suspension of 4-aminobenzoic acid (1,100 g, 0.73 mol), followed by batch addition of bromine (Br2, 38 mL, 0.73 mol). The reaction mixture was cooled to -10 °C and stirred for 2 hours while keeping the internal temperature below -5 °C. Upon completion of the reaction, the precipitate was collected by filtration and suspended in 350 ml of 1 M hydrochloric acid (HCl). The suspension was heated to reflux and maintained for 30 minutes. After rapid filtration, 150 ml of concentrated hydrochloric acid (HCl) was added to the hot filtrate to give 70 g (42% yield) of 2-aminobenzothiazole-6-carboxylic acid (white solid). The product was dried and used directly without further purification. | [References]
[1] Patent: US2009/123373, 2009, A1. Location in patent: Page/Page column 14-15 |
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