Structure of 21262-05-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 21262-05-5 |
| Formula : | C9H9Cl2NO |
| M.W : | 218.08 |
| SMILES Code : | CC(Cl)C(NC1=CC=C(Cl)C=C1)=O |
| English Name : | 2-Chloro-N-(4-chlorophenyl)propanamide |
| MDL No. : | MFCD04621521 |
* 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 |
|---|---|---|
| 68% | With aluminium trichloride In 1,2-dichloro-ethane for 16h; | |
| 41% | With H-ZSM-5 zeolite In 1,2-dichloro-ethane Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 92% | With potassium nitrate In sulfuric acid at 20℃; for 1h; | |
| 86% | With sulfuric acid; potassium nitrate at 0 - 20℃; for 1h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 99% | In toluene for 1h; Heating; | |
| 98% | In toluene at 120℃; for 1h; | |
| 88% | With potassium carbonate In acetone at 0 - 20℃; for 4h; | 5.1.1. General method for preparation of intermediates 9e11 and54-68 General procedure: 15.0 mmol (1 eq) of aniline (or a series of amines), and potassiumcarbonate (30 mmol, 2 eq) was dissolved in 60 mL acetone,and stirred in an ice bath to 0° C. 2-chloropropionyl chloride (2-bromobutyryl bromide or 2-bromoisobutyryl bromide 18.0 mmol,1.2 eq)was slowly added dropwise and stirred at room temperaturefor 4 h. The reaction mixture was quenched with water andextracted with ethyl acetate. The organic layer was washed withwater and brine successively, dried over anhydrous sodium sulfate,and concentrated in vacuum. The resulting residue was purified bysilica gel chromatography (petroleum ether/EtOAc 10/1) to givethe desired intermediates 9-11 and 54-68. |
| 86% | In N,N-dimethyl acetamide at 0 - 50℃; for 96h; | |
| In benzene Reflux; | ||
| With pyridine In chloroform at 20℃; for 12h; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: 92 percent / KNO3 / H2SO4 / 1 h / 20 °C 2: 90 percent / Fe; NH4Cl; AcOH / H2O; dimethylformamide / 0.25 h / 50 °C 3: 55 percent / NaI*2H2O; NaHCO3 / acetonitrile / 15 h / Heating | ||
| Multi-step reaction with 3 steps 1: 86 percent / sulfuric acid; potassium nitrate / 1 h / 0 - 20 °C 2: 56 percent / iron; ammonium chloride; acetic acid / H2O; dimethylformamide / 0.25 h / Heating 3: sodium iodide dihydrate; sodium hydrogen carbonate / acetonitrile / Heating |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: 92 percent / KNO3 / H2SO4 / 1 h / 20 °C 2: 90 percent / Fe; NH4Cl; AcOH / H2O; dimethylformamide / 0.25 h / 50 °C | ||
| Multi-step reaction with 2 steps 1: 86 percent / sulfuric acid; potassium nitrate / 1 h / 0 - 20 °C 2: 56 percent / iron; ammonium chloride; acetic acid / H2O; dimethylformamide / 0.25 h / Heating |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1: 92 percent / KNO3 / H2SO4 / 1 h / 20 °C 2: 90 percent / Fe; NH4Cl; AcOH / H2O; dimethylformamide / 0.25 h / 50 °C 3: 55 percent / NaI*2H2O; NaHCO3 / acetonitrile / 15 h / Heating 4: 62 percent / aq. H2O2 / aq. NaOH / 6 h / 60 °C | ||
| Multi-step reaction with 4 steps 1: 86 percent / sulfuric acid; potassium nitrate / 1 h / 0 - 20 °C 2: 56 percent / iron; ammonium chloride; acetic acid / H2O; dimethylformamide / 0.25 h / Heating 3: sodium iodide dihydrate; sodium hydrogen carbonate / acetonitrile / Heating 4: 83 percent / sodium hydroxide; hydrogen peroxide / H2O / 6 h / 60 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 5 steps 1: 92 percent / KNO3 / H2SO4 / 1 h / 20 °C 2: 90 percent / Fe; NH4Cl; AcOH / H2O; dimethylformamide / 0.25 h / 50 °C 3: 55 percent / NaI*2H2O; NaHCO3 / acetonitrile / 15 h / Heating 4: 62 percent / aq. H2O2 / aq. NaOH / 6 h / 60 °C 5: 65 percent / NaH / tetrahydrofuran / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 62.5% | In isopropyl alcohol for 2h; Reflux; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 81% | With potassium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 20h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 82% | With potassium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 20h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 56% | Stage #1: 4-phenyl-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiol With sodium In ethanol at 20℃; for 0.5h; Stage #2: 2-chloro-N-(4-chloro-phenyl)propionamide In ethanol for 6h; Reflux; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 84% | Stage #1: 5-mercapto-2-(pyridin-4-yl)-1,3,4-thiadiazole With sodium ethanolate In ethanol at 15℃; Stage #2: 2-chloro-N-(4-chloro-phenyl)propionamide In water at 20 - 65℃; for 8h; | 4.14 Synthesis of 2-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-ylthio)-N-(substituted)phenylacetamide 5a-h, 2-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-ylthio)-N-(substituted)phenylpropanamide 6aeh, 3-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-ylthio)-N-(substituted)phenylpropanamide 7aeh and 3-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-ylthio)-2-methyl-N-(substituted)phenylpropanamide 8aeh General procedure: To a cool solution of metallic sodium (1 mol) in an absoluteethanol; 5-(pyridin-4-yl)-1,3,4-thiadiazole-2-thiol (1 mol) (4) wasadded with stirring, at about 15 C. The solution was filtered. Theexcess of solvent was removed under suction and cold water wasadded to get a clear solution. The solution was again filtered toremove suspended particles. Then N-substituted-chloroalkylamide(1 mol) was added in small portion at room temperature withstirring, then stirring was continue between 60 and 65 C for 8 hcooled and extracted with EtOAc. The EtOAc layer was dried withsodium sulphate and the column purified. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 74% | With sodium hydroxide In ethanol; water at 20℃; for 4h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 60% | With sodium acetate In ethanol for 9.3h; Reflux; | General procedure for the alkylationof the thienotriazolopyrimidine 11yielding 12a,b, 16a-d, 17a-d, 18a-d General procedure: A mixture of the triazolo derivative 11 (0.36 g, 1mmol) and the appropriate alkyl iodide or α- and β-chloroamides(13a-d, 14a-d, 15a-d) (1.5 mmol) in the presenceof anhydrous sodium acetate (5 mmol) in absoluteethanol (70 mL) was heated under reflux till TLC indicatedcompletion of the reaction. The product precipitatedwas collected by filtration, dried and crystallized from theappropriate solvent. |