N-phenylbenzamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-phenylbenzamide (Structure II) is synthesized from aniline and benzoyl chloride using acetone as a reaction media and an aqueous solution of NaOH to neutralize the HCl generated. A 20 ml aqueous solution of NaOH (2.57 grams, 0.064 moles) and 6.0 grams (0.064 moles) of aniline are first added to a stirred 250 ml flask containing 75 ml of acetone. Benzoyl chloride (9.06 grams, 0.064 moles) is next added over a five minute period. This reaction mixture which now contains a white precipitate is stirred for 1.5 hours and then diluted with 50 ml of deionized water. This solution is next filtered and the filter cake obtained is sequentially washed with 50 ml of deionized water (two times) followed by 50 ml of methanol. The washed filter cake is recovered and DCS analysis of this product showed a sharp melting endotherm at 169° C. ##STR10## as a reaction media next filtered the filter cake obtained is sequentially washed with 50 ml of deionized water (two times) The washed filter cake is recovered at 169° C.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-phenylbenzamide (Structure II) is synthesized from aniline and benzoyl chloride using acetone as a reaction media and an aqueous solution of NAOH to neutralize the HCl generated. A 20 ml aqueous solution of NAOH (2.57 grams, 0.064 moles) and 6.0 grams (0.064 moles) of aniline are first added to a stirred 250 ml flask containing 75 ml of acetone. Benzoyl chloride (9.06 grams, 0.064 moles) is next added over a five minute period. This reaction mixture which now contains a white precipitate is stirred for 1.5 hours and then diluted with 50 ml of deionized water. This solution is next filtered and the filter cake obtained is sequentially washed with 50 ml of deionized water (two times) followed by 50 ml of methanol. The washed filter cake is recovered and DSC analysis of this product showed a sharp melting endotherm at 169° C. ##STR10## as a reaction media next filtered the filter cake obtained is sequentially washed with 50 ml of deionized water (two times) The washed filter cake is recovered at 169° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-phenylbenzamide (Structure II) is synthesized from aniline and benzoyl chloride using acetone as a reaction media and an aqueous solution of NAOH to neutralize the HCl generated. A 20 ml aqueous solution of NAOH (2.57 grams, 0.064 moles) and 6.0 grams (0.064 moles) of aniline are first added to a stirred 250 ml flask containing 75 ml of acetone. Benzoyl chloride (9.06 grams, 0.064 moles) is next added over a five minute period. This reaction mixture which now contains a white precipitate is stirred for 1.5 hours and then diluted with 50 ml of deionized water. This solution is next filtered and the filter cake obtained is sequentially washed with 50 ml of deionized water (two times) followed by 50 ml of methanol. The washed filter cake is recovered and DSC analysis of this product showed a sharp melting endotherm at 169° C. ##STR10## as a reaction media next filtered the filter cake obtained is sequentially washed with 50 ml of deionized water (two times) The washed filter cake is recovered at 169° C.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction tube containing 1-iodo-2-nitrobenzene (124 mg, 0.5 mmol), N-phenylbenzamide (118 mg, 0.6 mmol), CuI (4.8 mg, 0.025 mmol), N-methylethylenediamine (4.4 μL, 0.05 mmol), potassium phosphate (212 mg, 1 mmol) in dry toluene (1.5 mL) was purged with dry argon for 3 min. After heating at 100° C. for 18 h, the iron powder (10 mol.-eq.) and glacial acetic acid (5 mL) are directly added. Then the reaction mixture is heated at reflux for 30 min. An additional 10 mol.-eq. of iron powder are added and the reaction mixture is heated at reflux for further 30 min. The solvents were removed under reduced pressure and the crude was extracted with ethyl acetate against saturated sodium bicarbonate solution. The organic phase was dried and the solvent was removed on a rotary evaporator. Then the residue was purified by preparative HPLC, affording the title compound as a solid (90 mg, 67% yield). was purged with dry argon for 3 min Then the reaction mixture is heated at reflux for 30 min the reaction mixture is heated at reflux for further 30 min The solvents were removed under reduced pressure the crude was extracted with ethyl acetate against saturated sodium bicarbonate solution The organic phase was dried the solvent was removed on a rotary evaporator Then the residue was purified by preparative HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared with the analogous procedure described in example 1 using 1-Iodo-2-nitrobenzene (125 mg, 0.5 mmol) and benzanilide (118 mg, 0.6 mmol) as starting materials to yield the title compound as pale yellow solid (95 mg, 70%). mp 105-107° C. 1H NMR (DMSO) δ 7.24 (d, J=7.9 Hz, 1 H), 7.35-7.62 (m, 12 H), 7.84 (d, J=7.6 Hz, 1 H); 13C NMR δ 111.0, 118.1, 123.7, 124.1, 127.5, 127.9, 128.4, 129.2, 129.3, 130.0, 130.2, 135.5, 136.2, 139.3, 151.3. HRMS (FAB): cal. for C19H15N2 [M+H+]: 271.1235; found: 271.1230. The title compound was prepared with the analogous procedure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of mono-methyl terephthalate (4.00 g, 22 mmol) in ethyl acetate (25 mL) and DMF (0.1 mL) was cooled in an ice bath and treated with oxalyl chloride (11 mL, 2N in CH2Cl2, 22 mmol) over 30 minutes. After stirring 2 hours at room temperature the solvent was removed on a rotary evaporator and the residue dissolved in CH2Cl2 (20 mL) and added to a solution of benzyl 4-aminobenzoate (5.00 g, 22 mmol) in CH2Cl2 (25 mL) and triethylamine (4.3 mL, 31 mmol) at −60° C. The reaction mixture was warmed to room temperature for 1 hour and then partitioned between water and ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, filtered, and evaporated. The residue was recrystallized from t-butyl methyl ether to give 5.85 g of compound 8. was removed on a rotary evaporator the residue dissolved in CH2Cl2 (20 mL) The reaction mixture was warmed to room temperature for 1 hour partitioned between water and ethyl acetate The ethyl acetate layer was dried over sodium sulfate filtered evaporated The residue was recrystallized from t-butyl methyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 830 mg (2.44 mmole) of the aniline compound obtained in step 1 was dissolved in 10 mL of pyridine, 0.340 mL (2.93 mmoles) of benzoylchloride was added, and the mixture was stirred overnight at room temperature. When the reaction had ended, the solvent was removed under reduced pressure. Ethyl acetate and 1N HCl aqueous solution were added to the residue. The mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure, yielding 1.11 g of N-benzoylaniline compound. the solvent was removed under reduced pressure Ethyl acetate and 1N HCl aqueous solution were added to the residue The mixture was extracted with ethyl acetate The obtained organic layer was washed with saturated brine dried with anhydrous sodium sulfate The solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 830 mg (2.44 mmole) of the aniline compound obtained in step 1 was dissolved in 10 mL of pyridine, 0.340 mL (2.93 mmoles) of benzoylchloride was added, and the mixture was stirred overnight at room temperature. When the reaction had ended, the solvent was removed under reduced pressure. Ethyl acetate and 1N HCl aqueous solution were added to the residue. The mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure, yielding 1.11 g of N-benzoylaniline compound. the solvent was removed under reduced pressure Ethyl acetate and 1N HCl aqueous solution were added to the residue The mixture was extracted with ethyl acetate The obtained organic layer was washed with saturated brine dried with anhydrous sodium sulfate The solvent was removed under reduced pressure