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CAS No. : | 216082-34-7 | MDL No. : | MFCD11149391 |
Formula : | C10H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XGBGUOKFVIRIKH-UHFFFAOYSA-N |
M.W : | 193.20 | Pubchem ID : | 28561351 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
66% | With sodium chlorite; recorcinol In water; <i>tert</i>-butyl alcohol at 30 - 40℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 60 percent / K2CO3 / dimethylformamide / 2 h / 92 - 96 °C 2: ethanol / 120 h / 20 °C 3: 75 percent / aq. HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol / 120 h / 20 °C 2: 75 percent / aq. HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; dichloromethane at 20℃; for 16h; | 6 (2-Formyl-phenoxy)-acetic acid (0.5 mmol) is dissolved in 1 mL of CH2Cl2. Oxalyl chloride (0.066 mL) is added along with one drop of DMF. After 1 hour, the solvent is removed from the mixture. The resultant residue is dissolved in 1 mL of CH2Cl2 and added to 1 mL of NH2 Me in THF (2 M) at ambient temperature. After 16 hours of stirring, the solvent is removed and the mixture is purified by preparative TLC (10% MeOH/EtOAc) to yield the product 2-(2-formyl-phenoxy)-N-methyl-acetamide as an off white solid: LC/MS (ES+): 194.1 (M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane for 0.166667h; | 6 The 2-(2-formyl-phenoxy)-N-methyl-acetamide (0.0311 mmol) is added to 4-chloro-thiobenzoic acid hydrazide (0.0342 mmol) in 0.1 mL of CH2Cl2. After 10 minutes, DIEA (0.05 mL) and 2,4,6-trifluoro-benzoyl chloride (0.0467 mmol) are added. The mixture is kept at room temperature overnight. After removal of solvent, the residue is purified by preparative HPLC (20-100% MeCN/H2O gradient) to give the product 2-{2-[5-(4-chloro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-N-methyl-acetamide as an off white solid: LC/MS (ES+): 520.1 (M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: L-1-methyl-2-cyclohexylethylamine; 2-(2-formyl-phenoxy)-N-methyl-acetamide In methanol at 100℃; for 2h; Stage #2: With methanol; sodium tetrahydroborate at 60℃; for 6h; | 7.B Step B Aldehyde 3 (0.55 mmol), amine 4 (0.5 mmol) were dissolved in 0.6 ml MeOH, heated at 100° C for 2 hours, then mixture was cooled, NaBH4 (0.5 mmol) was added and stirred for 4 hours. The mixture was heated for 2 hours at 60° C, 3 ml of methanol and 0.2 g of C-18 chromatographic phase were added, stirred for 2 hours, filtered, evaporated and optionally dissolved in 0.5 mL of DMSO. The residue was purified using HPLC. Yield: 24- 47%. (0743) [00304] 8.56 (s, 1H), (0744) 7.19 (t, J = 8.0 Hz, 2H), 6.93 - 6.84 (m, 2H), 4.51 (s, 2H), 3.78 (d, J = 12.0 Hz, 1H), 3.65 (d, J = 12.1 Hz, 1H), 2.71 (d, J = 5.8 Hz, 2H), 2.66 (d, J = 4.6 Hz, 3H), 2.54 (s, 1H), 1.67 (d, J = 15.3 Hz, 5H), 1.35 (s, 1H), 1.20 (dd, J = 22.0, 9.6 Hz, 2H), 1.05 (d, J = 6.2 Hz, 3H), 0.86 (d, J = 12.3 Hz, 2H). |