2,5-Dichlorobenzamide

General synthetic procedure: Cyanoguanidine 2 (0.084 g, 1 mmol) is suspended in 2 mL of neat aromatic substrate (alternatively, the arene may be suspended in CHGeneral procedure: To a clean oven-dried 15 mL sealed tube equipped with magnetic stir bar, benzamide (0.25 mmol, 1.0 equiv), Pd(OAc)2 (5.0 mol%, 2.8 mg), and NXS (0.3 mmol, 1.2 equiv.) were added sequentially. DCE (2.0 mL) was then added to the reaction mixture followed by trifluoroacetic acid (475 muL). The tube was tightly closed and placed in a preheated oil bath of 60 C and stirred for 24 h. In each case, the reaction was monitored by TLC, and after completion, the reaction mixture was cooled to room temperature. The solvent was evaporated under reduced pressure and then diluted with ethyl acetate followed by neutralization with a saturated solution of sodium bicarbonate. After extraction with ethyl acetate (15 mL×3), the organic layer was washed with brine solution and dried over sodium sulphate. After evaporation of the solvent, the crude mixture was purified by column chromatography silica gel using ethyl acetate/hexanes as the eluent.General procedure: A solution of thionyl chloride (25 mmol) was addeddropwisely to 1 (20 mmol) in toluene(15 mL). The mixture was heated to reflux for 3 h. Excess thionyl chloride wasremoved in vacuo. The remained mixture was added dropwise to ammonia waterbelow 10 C, then stirred at 10 C for 1 h. The intermediate 3 was obtained as white solid by filtration.General procedure: Oxalylchloride (30 mmol) was added dropwise to a solution of 3 (10 mmol) in 1, 2-dichloroethane(25 mL) and the mixture was heated to reflux for 6h under nitrogen atmosphere.Excess oxalylchloride and 1, 2-dichloroethane was evaporated under reducedpressure to afford the crude intermediate4.General procedure: Oxalyl chloride (6.8 mmol) was added to a solution of substituted 2-halogenbenzamide (4 mmol) in 1, 2-dichloroethane (10 mL). The reaction mixture was heated to reflux for 3 h. The solvent was evaporated under reduced pressure. Acetone (15 mL) was added to the residue and then cooled to 25C. Secondary amine was dissolved in acetone (5 mL) and then added to the above solution. Keeping the reaction under 25C for 0.5 h, the precipitated solid was filtered, washed with a small amount of acetone, and dried to give the target compounds in excellent yields (84-96%).General synthetic procedure: Cyanoguanidine 2 (0.084 g, 1 mmol) is suspended in 2 mL of neat aromatic substrate (alternatively, the arene may be suspended in CH2Cl2) and freshly distilled triflic acid (0.5 mL, 6 mmol) is slowly added. The mixture is stirred at 60 C for 2 h, after which 1 mL of cold water is added to the solution. The mixture is then stirred overnight. Product isolation is accomplished with basification of the mixture using 10 M NaOH and extraction of the mixture twice with chloroform. The organic extracts are washed with water, and then brine, and dried with anhydrous MgSO4. Crude products may be further purified by silica gel column chromatography (hexanes:ethyl acetate).

Molecular Weight:190.02
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:188.9748192
Monoisotopic Mass:188.9748192
Topological Polar Surface Area:43.1
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes