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CAS No. : | 59813-89-7 | MDL No. : | MFCD00656934 |
Formula : | C9H10N2S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 210.32 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; tin(ll) chloride | ||
With hydrogenchloride; iron |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) NaNO2, aq. HCl, H2O, (ii) /BRN= 507757/, NaOAc, CuCl2, acetone; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6-Amino-2-merkaptobenzothiazol, Alkylhalogenid; | ||
entspr. 2-Mercaptobenzothiazol, C2H5J; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetone; NaHCO3 2: aqueous HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol 2: SnCl2; aqueous HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) NaNO2, aq. HCl, H2O, (ii) /BRN= 507757/, NaOAc, CuCl2, acetone 2: (i) (heating), (ii) /BRN= 168150/, Ac2O, Et3N |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 24h; | Synthesis of 2-ALKYLSULFANYL-BENZOTHIAZOL-6-YL-AMINE To a solution of 6-amino-2-merceptobenzothiazole (273mg, 1.5 MMOL) in anhydrous THF (10 mL) was added NaH (60% dispersion, 1.5 mmol), followed by alkyl halide (1.5 MMOL). The mixture was stirred at rt for 24h, partitioned between ethyl acetate and 5% sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to a yellow solid, which was purified with recrystallization or flash chromatography. (Yield 60-90%). The following amines were synthesized with the method described above: 2-Ethylsulfanylbenzothiazol-6-ylamine Yellow crystalline solid. mp 77-78°C (lit. 77°C). TLC single spot at Rf 0.78 (8% methanol/DCM) ;'H NMR (270 MHz, DMSO): 5 7.50 (1H, d, J = 8.5 Hz, 4-H), 6.98 (1H, d, J = 2.2 Hz, 7-H), 6.69 (1 H, dd, J = 8. 5,2. 2 Hz, 5-H), 5.33 (2H, broad, NH2), 3.23 (2H, q, J = 7.3 Hz, SCH2), 1.35 (3H, t, J = 7. 3 Hz, CH3). (Francolor, S. A.; US 2500093; 1945) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: 3-chloro-2-methylbenzenesulfonyl chloride With pyridine In dichloromethane at 20℃; for 0.166667h; Stage #2: 6-amino-2-ethylthiobenzothiazole In dichloromethane at 20℃; for 4 - 16h; | To a solution arylsulphonyl chloride (1.1 eq. ) in DCM (5-10 mL) were added pyridine (2.2 eq. ) and catalytic amount of DMAP. The solution was stirred at room temperature under nitrogen for 10 minutes. Then the amine (1 eq. ) was added and the reaction mixture was stirred at room temperature under nitrogen for 4-16 hrs. The resulting mixture was partitioned between DCM and 5% sodium bicarbonate. The organic layer was washed with brine, dried over MGSO4, and concentrated to give a yellow residue. The crude compound was then purified by flash chromatography to give desired BENZENESULPHONAMIDE as crystalline solid. (Yield 40-90%).; 3-CHLORO-N- (2-ETHYLSULFANYLBENZOTHIAZOL-6-YL)-2-METHYLBENZENESULPHONAMIDE (STX751, XDS01141) Off-white solid (220 mg; 55%). TLC single spot at Rf: 0.83 (17% EtOAc/DCM); HPLC purity 96% (tR 1.9 min in methanol) ;'HNMR (400MHZ, DMSO-d6) 5 10.8 (1H, s, NH), 7.89 (1H, dd, J = 8.0, 1.0 Hz, 6'-H of benzene), 7.71 (1H, d, J = 8 Hz, 4-H of benzothiazole), 7.70 (1H, d, J = 2 Hz, 7-H of benzothiazole), 7.70 (1H, dd, J = 8.0, 1.0 Hz, 4'-H of benzene), 7.36 (1H, t, J = 8 Hz, 5'-H of benzene), 7.15 (1H, dd, J = 8.0, 2.0 Hz, 5-H of benzothiazole), 3.30 (2H, q, J = 7.0 Hz, SCH2), 2.66 (3H, s, CH3), 1.38 (3H, t, J = 7.0 Hz, CH3) ; APCI-MS 397.99 (M) + ; FAB-HRMS CA) CD for C16H16CIN202S3 (MH+) 399.0062, found 399.0048. |