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CAS No. : | 91447-89-1 | MDL No. : | MFCD10686940 |
Formula : | C6H5ClN2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 172.64 | 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 |
---|---|---|
97% | With triethanolamine; hydrogen sulfide In ethanol | 2.a Example 2; Step a To a SOLUTION/SUSPENSION of 1 (10. 0 g; 72 mmol) in ethanol (100 mL) was added TRIETHANOLAMINE (4.0 mL; 39. 8 mmol). H2S was then passed through the solution. After a few minutes precipitation of a yellow solid was observed. The reaction was continued until TLC showed complete conversion (30 min). The reaction mixture was poured into ice-water (-300 mL), which resulted in precipitation of product. After stirring for 15 min the solid was filtered off, washed with water and dried (vacuum, P205). YIELD : 12. 1 g (97%). |
With triethanolamine; ethanol; hydrogen sulfide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 150℃; for 0.116667h; | 40 Example 40; Ethyl 5-[2-(2-chloro-(4-pyridyl))(1,3-thiazol-4-yl)-2-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate A mixture of ethyl 5-(2-bromo-acetyl)-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (Example 24c) (0.20 g, 0.66 mmol) and 2-chloroisothionicotinamide (0.18 g, 0.86 mmol) in EtOH (6 ML) was heated at 150° C. by microwave for 7 min.The solid was filtered and triturated with MeOH, filtered and dried by air to give a light yellow solid. MS (m+2): 377.4. Calc'd for C17H14ClN3O3S Exact Mass: 375.04. MP: 250° C. (dec). | |
In ethanol at 80℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: POCl3; PCl5 2: ethanol; tris-<2-hydroxy-ethyl>-amine; H2S |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: aqueous H2O2; acetic acid 2: POCl3; PCl5 3: ethanol; tris-<2-hydroxy-ethyl>-amine; H2S |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine | 7 Compounds in example 7 may be prepared in a similar manner as those described in Example 5: the thioamide of 2-chloroisonicotinamide [prepared according to Libermann, D ; Rist, N.; Grumbach, F.; Cals, S.; Moyeux, M.; Rouaix, A. Memoires Presentes a la Societe Chimique 1958, 694-702] is alkylated with methyl iodide. The resulting thioimidate salt (4.3 g, 13.5 mmol) is stirred overnight in 100 ml isopropanol with 1.7 g ammonium acetate. After concentration and trituration with isopropanol/t-BuOMe, filtration provides the amidine as a solid (2.3 g). This material is stirred overnight with 3.5 g solid NaHCO3, 2.4 ml of a 50% aqueous solution of H2NCN, 40 ml isopropanol, and 1100 ml H2O. The resulting precipitate is triturated with a small amount of isopropanol to obtain 1.6 g cyanoamidine 1170. This material is suspended in CH2Cl2/CH3CN with 1.3 ml POCl3 and 1 ml DMF at 0° C. and the mixture is warmed to room temperature. After several hours, the homogenous solution is poured into a 1:1 mixture of pH 7 buffer and saturated NaHCO3. After extraction with EtOAc and filtration through a plug of silica, 1.6 g of 2-chloro-4-(2-chloro-pyridin-4-yl)-[1,3,5]triazine 1171 is obtained as a white solid. MS m/z=227 [M+H]+; HPLC Rt=13.18 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In acetone for 72h; in the dark; | 2.b Step b To a solution of 2 (7.0 g; 40.6 mmol) in acetone (170 mL) was added iodomethane (12. 6 mL; 202 mmol) and the reaction mixture was stirred in the dark for 3 days. The yellow precipitate was filtered off and washed with acetone and ether (2x) and dried. Yield: 8. 57 g (67%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Lawessons reagent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 80℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; | 4.5. 2-(2-Chloropyridin-4-yl)-4-(pyridin-3-yl)thiazole (11) Thioamide 10 (60.0 mg, 0.35 mmol), 3-(bromoacetyl)pyridine hydrobromide (7, 98 mg, 0.35 mmol), and cesium carbonate (170 mg, 0.52 mmol) were added to dry DMF (10 mL). The reaction mixture was heated at 100 °C for 8 h and then allowed to cool and then quenched with distilled water (30 mL). The organic materials were extracted with ethyl acetate (30 mL). The organic layer was isolated and dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure. The solid residue was purified by silica gel flash chromatography, using ethyl acetate-hexane (1:1), and then dichloromethane-methanol (95:5) to yield a yellowish-white solid (64 mg, 67%): mp 182-183 °C. 1H NMR (DMSO-d6) δ 9.28 (s, 1H), 8.56 (m, 3H), 8.42 (d, J = 7.2 Hz, 1H), 8.10 (s, 1H), 8.01 (d, J = 7.0 Hz, 1H), 7.52 (dd, J = 3.9, 7.2 Hz, 1H); 13C NMR (DMSO-d6) δ 164.22, 154.03, 152.41, 152.06, 150.36, 148.35, 143.52, 134.50, 130.11, 124.88, 121.19, 120.72, 120.06; ESIMS (m/z, rel intensity) 274/276 (MH+, 100/24); HRMS (ESI), m/z MH+ 274.0201, calcd for C13H8ClN3S 274.0206; HPLC purity (C-18 reverse phase column): 98.93% (methanol-H2O, 95:5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 8 h / 100 °C 2: methanol / 24 h / 120 °C / Sealed tube |