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CAS No. : | 284673-69-4 | MDL No. : | MFCD01764385 |
Formula : | C10H8Cl2N2OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 275.15 | 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 |
---|---|---|
Stage #1: 2-bromo-1-(3,5-dichloro-2-methoxy-phenyl)-ethanone; thiourea In ethanol at 165℃; for 0.0833333h; Microwave iiradiation; Stage #2: With sodium hydroxide In water | 2.A 2-Bromo-1-(3,5-dichloro-2-methoxy-phenyl)-ethanone (200 mg, 0.746 mmol), thio-urea (100 mg, 1.3 mmol) in ethanol (2 mL) and heated to 165° C. for 300 s in a Emrys optimizer EXP microwave. The volatile solvent was removed and the residue dissolved in water and adjusted to pH 7 with sodium hydroxide. The aqueous mixture was extracted with ethyl acetate (3×50 mL), and evaporated to dryness to give a oily residue. This was then used without further purification in the next step. | |
In ethanol at 165℃; for 0.0833333h; Microwave irradiation; | 2.A Example 2. 2-Benzimidazol-1-yl-N-r4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-yll-acetamide A: 4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-ylamine 2-Bromo-1-(3,5-dichloro-2-methoxy-phenyl)-ethanone (200mg, 0.746mmol), thiourea (100mg, 1.3mmol) in ethanol (2ml_) and heated to 165 0C for 300s in a Emrys optimizer EXP microwave. The volatile solvent was removed and the residue dissolved in water and adjusted to pH 7 with sodium hydroxide. The aqueous mixture was extracted with ethyl acetate (3 x 5OmL), and evaporated to dryness to give a oily residue. This was then used without further purification in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | Stage #1: 2-(1H-benzo[d]imidazol-1-yl)acetic acid With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide; toluene at 20℃; for 24h; Stage #2: 4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-ylamine In N,N-dimethyl-formamide; toluene at 20℃; for 24h; | 2.B (1H-Benzimidazol-1-yl)acetic acid (50 mg, 0.28 mmol) (Example 1B) was dissolved in toluene and N,N-dimethylformamide. Triethylamine (0.03 mL, 0.42 mmol) then added followed by diphenyl phosphoryl azide (DPPA) (0.07 mL, 0.36 mmol) and stirred at room temperature for 24 h. 4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-ylamine (57 mg, 0.21 mmol) (Example 2A) was then added in one portion and the mixture stirred for 24 h at room temperature. Mixture was evaporated to dryness and DMSO (1 mL) added before purification by preparative LCMS to give an oily residue (8.9 mg, 7%). 1H NMR (400 MHz, CD3OD) δ ppm 3.81 (3H, s), 5.34 (2H, s), 7.29-7.36 (3H, m), 7.42 (1H, d, J=2.5 Hz), 7.53 (1H, d, J=7.2 Hz), 7.72 (1H, d, J=7.1 Hz), 8.06 (1H, d, J=2.6 Hz), 8.25 (1H, s). MS (ES) m/z: 434.3 [M+H]. |
7% | Stage #1: 2-(1H-benzo[d]imidazol-1-yl)acetic acid With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide; toluene at 20℃; for 24h; Stage #2: 4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-ylamine In N,N-dimethyl-formamide; toluene at 20℃; for 24h; | 2.B B: 2-benzimidazol-1-yl-N-r4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-yll-acetamide (1 H-Benzimidazol-1-yl)acetic acid (50mg, 0.28mmol) (Example IjJ) was dissolved in toluene and λ/,λ/-dimethylformamide. Triethylamine (0.03ml_, 0.42mmol) then added followed by diphenyl phosphoryl azide (DPPA) (0.07ml_, 0.36mmol) and stirred at room temperature for 24h. 4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-ylamine (57mg, 0.21 mmol)(Example 2A) was then added in one portion and the mixture stirred for 24h at room temperature. Mixture was evaporated to dryness and DMSO (1 mL) added before purification by preparative LCMS to give an oily residue (8.9mg, 7%). 1H NMR (400MHz, CD3OD) δ ppm 3.81 (3H, s), 5.34 (2H, s), 7.29-7.36 (3H, m), 7.42 (1 H, d, J = 2.5Hz), 7.53 (1 H, d, J = 7.2Hz), 7.72 (1 H, d, J = 7.1 Hz), 8.06 (1 H, d, J = 2.6Hz), 8.25 (1 H, s). MS (ES) m/z: 434.3 [M+H]. |