Structure of 17700-54-8
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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. : | 17700-54-8 |
| Formula : | C8H7Cl2NO |
| M.W : | 204.05 |
| SMILES Code : | CC(NC1=C(Cl)C=CC=C1Cl)=O |
| English Name : | N-(2,6-Dichlorophenyl)acetamide |
| MDL No. : | MFCD00013629 |
* 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 chlorosulfonic acid |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With acetic acid; calcium chloride |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 96% | In acetic acid | 1.A A. A. 2,6-Dichloroacetanilide To a mechanically stirred solution of 2,6-dichloroaniline (76 g, 0.047 mol) in 60 mL of glacial acetic acid is added dropwise acetyl chloride (36 mL, 0.5 mol). After the addition is complete, the reaction mixture is heated at 90° C. for 20 minutes. The solution is poured into ice water (500 mL), forming a white precipitate. The solids are filtered, washed with water and dried to give the product (91.8 g, 96%, white solid, m.p. 179°-180° C., lit. m.p. 180°-181° C. from glacial acetic acid). NMR (CDCl3, 200 MHz): δ 2.22 (s, 3H, CH3 CO), 7.06 (broad, 1H, NH), 7.14-7.45 (m, 3H, ArH). |
| 78% | In acetic acid at 70℃; for 0.5h; | |
| With acetic acid |
| With acetic acid at 100℃; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In toluene for 5h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With copper; potassium carbonate at 160℃; for 96h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 100% | With pyridine for 4h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 98.8% | In ethyl acetate at 70℃; for 0.5h; | 1.S1; 8; 15.S1; 16.S1; 17.S1; 38.S1; 39.S1; 40.S1; 41.S1; 42.S1 S1. Weigh 0.2 mol (32.40 g) of compound I and 0.21 mol (21.44 g) of acetic anhydride (ie, acylation protection reagent), dissolve them in 100 mL of ethyl acetate, heat to 70±5 °C with refluxing and stir, and react for 0.5 h. , the basic reaction is complete, the ethyl acetate is concentrated under reduced pressure to 10 mL, the ethyl acetate is recovered, and then poured into 200 mL of 5 ice water, filtered and the filter residue is retained, and dried to obtain a white solid compound, which is compound II. |
| 98.8% | In ethyl acetate at 70℃; for 0.5h; Large scale; | 1.S1; 15.S1; 16.S1; 17.S1; 38.S1; 39.S1; 40.S1; 41.S1; 42.S1 S1. Weigh 0.2 mol (32.40 g) of compound I and 0.21 mol (21.44 g) of acetic anhydride (ie, acylation protection reagent), dissolve them in 100 mL of ethyl acetate, heat to 70±5 °C with refluxing and stir, and react for 0.5 h. , the basic reaction is complete, the ethyl acetate is concentrated under reduced pressure to 10 mL, the ethyl acetate is recovered, and then poured into 200 mL of 5 ice water, filtered and the filter residue is retained, and dried to obtain a white solid compound, which is compound II. |
| 97% | With supported L-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate on Silica Gel at 20℃; for 1.2h; Green chemistry; |
| 50% | With glacial acetic acid; zinc for 0.5h; Ambient temperature; | |
| 47.64% | With 4-dimethylaminopyridine In dichloromethane at 0 - 40℃; | 15 Synthesis o/iV-(, 6-thchiorophenyace tam/dc: Into a 250 rnL round-bottom flask was added 2,6-dichioroaniline (20 g, 123.45 mmol, I equiv), DMAP(3.0 g, 2469 mmol, 0.20 equiv) and DCM (100 mL) at room temperature. Then the resulting mixture was cooled at 0 °C. To a stirred mixture was added Ac20 (37. 8 g, 37035 mmol, 3.00 equiv) in portions over 10 miii at 0°C. Then the resulting mixture was stirred for overnight at 40°C. The resulting mixture was extracted with EA. The organic layers were combined and washed with water and brine, dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography, eluted with PE/EtOAc (90/10) to afford the title compound (12g. 47.64%) as an off-white solid. Analytical Data: LC-MS: (ES, m/z): RT:=0.839 miii, m/z :::204[M ±Fi] |
| With pyridine for 2h; Heating; | ||
| With sulfuric acid |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 78% | With thionyl chloride In diethyl ether for 1h; T < 5 deg C; | |
| 78% | With thionyl chloride In benzene 0-5 deg C for 20 min, then further 30 min and 25 deg C for 1 h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate 1.) toluene, 30-35 deg C, 30 min, 2.) toluene, 30-35 deg C, 1 h; Yield given. Multistep reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| (i) ClSO3H, (ii) N2H4*H2O; Multistep reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Rk. mit 1) Chlorsulfonsaeure, 2) Hydrazinhydrat --> 3,5-Dichlor-sulfanilhydrazid; |