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Chemical Structure| 95-26-1 Chemical Structure| 95-26-1

Structure of 95-26-1

Chemical Structure| 95-26-1

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Product Details of [ 95-26-1 ]

CAS No. :95-26-1
Formula : C9H9NS
M.W : 163.24
SMILES Code : CC1=CC=C(SC(C)=N2)C2=C1
English Name :2,5-Dimethylbenzo[d]thiazole
MDL No. :MFCD00005796
InChI Key :XHANCLXYCNTZMM-UHFFFAOYSA-N
Pubchem ID :7227

Safety of [ 95-26-1 ]

Application In Synthesis of [ 95-26-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 95-26-1 ]

[ 95-26-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 95-26-1 ]
  • [ 650635-66-8 ]
  • [ 686747-49-9 ]
YieldReaction ConditionsOperation in experiment
Nitrierung;
With sulfuric acid; nitric acid In water at -5 - 0℃; for 2h; To a solution of 2, 5-dimethylbenzothiazol (1.63 g, 10 MMOL) in Conc. H2SO4 (12 mL) was added HN03 (69%, 1 MMOL) AT-5°C. After stirred AT-5-0°C for 2h, the mixture was poured over ice-water (150 mL). The precipitate was collected and washed with 5% sodium bicarbonate, water and 70% ethanol. The product (1.98 g) was a mixture of 4- nitro-2, 5-dimethylbenzothiazol and 6-nitro-2, 5-dimethylbenzothiazol in 1: 1 ratio judged by NMR. The product (998 mg) was hydrogenated over 5% Pd/C (600 mg) in ethanol- THF (50: 20 mL) at atmosphere pressure to give a yellow solid (880 mg). Separation with flash chromatography (EtOAc/DCM gradient elution) yielded 2,5- dimethylbenzothiazol-4-ylamine as yellow crystals (400 mg). TLC single spot at Rf 0.60 (15% EtOAc/DCM) ;'H NMR (270 MHz, DMSO): õ 7.05 (1H, d, J = 8.0 Hz, ArH), 6.99 (1H, d, J. = 8.0 Hz, ArH), 5.26 (2H, s, NH2), 2.74 (3H, s, CH3), 2.18 (3H, s, CH3) ; APCI- MS 177 (M-H) +. 2, 5-Dimethylbenzothiazol-6-ylamine was obtained as yellow solid (320 mg). TLC single spot at RF 0. 55 (15% EtOAc/DCM) ;'H NMR (270 MHz, DMSO): õ 7.47 (1H, s, ArH), 7.05 (1H, s, ArH), 5.05 (2H, s, NH2), 2.65 (3H, s, CH3), 2.16 (3H, s, CH3) ; APCI-MS 177 (M- H) +.
  • 2
  • [ 95-26-1 ]
  • [ 650635-66-8 ]
YieldReaction ConditionsOperation in experiment
92% With sulfuric acid; nitric acid at 20℃; for 2h;
  • 3
  • [ 95-26-1 ]
  • [ 650635-67-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / HNO3; H2SO4 / 2 h / 20 °C 2: 70 percent / SnCl2; aq. HCl / 2 h / 60 °C
  • 4
  • [ 95-26-1 ]
  • [ 686747-14-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Nitrierung 2: SnCl2; aqueous HCl
Multi-step reaction with 2 steps 1: Nitrierung 2: SnCl2; aqueous HCl
Multi-step reaction with 2 steps 1: potassium nitrate||KNO3||NO3K / dimethyl sulfoxide / 0.17 h / -5 - 20 °C 2: dichloro-λ2-stannane dihydrate / ethyl acetate / 2 h / 50 - 60 °C
  • 5
  • [ 95-26-1 ]
  • [ 20061-46-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,5-dimethylbenzothiazole With tetrachloromethane; N-Bromosuccinimide at 80℃; for 4h; UV-irradiation; Stage #2: With hexamethylenetetramine; acetic acid In water at 110℃; for 2h; 8 Example 8: Preparation of benzothiazolephosphonium compound L34 and 14-epoxybenzo thalidone compound HH8 [Show Image] To a solution of dimethylbenzothiazole (Fluka, Buchs) (8 g) in 50ml tetrachloromethane is added N-bromosuccinimide (10.5g), the solution is radiated with a tungsten lamp and heated for 4 hours to 80°C. The resulting mixture is cooled to room temperature, and then filtered, solvent is evaporated. The thus obtained oily matter is mixed with 50% acetic acid aqueous solution (100ml) and hexamethylenetetramine (23.4 g), the mixtue is heated for 2 hours to 110°C. Reaction is then stopped by adding water, and extracted with ethyl acetate. The collected extracts are sequentially extacted with saturated NaHCO3, water, and brine water, dried over Na2SO4, filtered and evaporated to dry. The product is obtained after purified by SiO2 chromatography.
  • 6
  • [ 95-26-1 ]
  • [ 1312684-56-2 ]
  • [ 178396-28-6 ]
YieldReaction ConditionsOperation in experiment
6.61% Stage #1: 2,5-dimethylbenzothiazole With bromine In chloroform Reflux; Stage #2: With sodium hydroxide In chloroform at 20℃; 2.1 A mixture of 2,5-dimethyl-l,3-benzothiazole (10.00 g, 61.26 mmol, Aldrich)and bromine (6.94 mL, 134.8 mmol) in chloroform (200 mL) was heated at reflux overnight. After cooling to room temperature, the mixture was washed with 1 N NaOH, followed by saturated sodium thiosulfate and brine, then dried over sodium sulfate and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 50% EtOAc in hexane. The first peak had a retention time of 2.51 minutes, LCMS calculated for C9H9BrNS(M+H)+: m/z = 242.0; found: 241.9. 1H NMR shown to be the desired product B (980 mg, 6.61%). 1H NMR (CDC13, 400 MHz) 7.63 (1H, d, J= 8.4 Hz), 7.22 (1H, d, J= 8.4 Hz), 2.87 (3H, s), 2.55 (3H, s) ppm. The second peak had a retention time of 2.758 minutes, LCMS (M+H)+ m/z = 241.9; found: 242. 1H NMR showed no coupling for the two phenyl hydrogens confirming the 6-bromo isomer.
  • 7
  • [ 512-56-1 ]
  • [ 791614-90-9 ]
  • [ 95-26-1 ]
YieldReaction ConditionsOperation in experiment
67% With copper(l) iodide; lithium iodide; lithium tert-butoxide at 50℃; for 16h; Inert atmosphere;
 

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