N,N-Diphenylformamide

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

Procedure: A mixture of 2-(3-iodobenzoyl)acetonitrile (36.2 g, 133.5 mmol) and N,N-diphenylformamide (26.2 g, 133.5 mmol) in toluene (200 ml) was heated at reflux under a nitrogen atmosphere. After 8 h, the reaction mixture was cooled to room temperature and diluted with ether (200 ml) to give 2-(3-iodobenzoyl)-3-phenylaminoacrylonitrile (31.2 g) as a solid. was heated at reflux under a nitrogen atmosphere

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

Procedure: By essentially the procedure of Example 1, a tube was charged with 40 g of methyldiphenylamine and 2.0 g CuCl2. 2H2O. The reaction was run at 115°-125° C. for 2 hr at 290-400 psi. About 0.1 mole of oxygen was injected incrementally. GC/MS analysis showed a 98.6% conversion of methyldiphenylamine and a 43.3% yield of diphenylformamide.

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

Procedure: By essentially the procedure of Example 1, a tube was charged with 40 g of methyldiphenylamine and 2.0 g CuCl2. 2H2O. The reaction was run at 115°-125° C. for 2 hr at 290-400 psi. About 0.1 mole of oxygen was injected incrementally. GC/MS analysis showed a 98.6% conversion of methyldiphenylamine and a 43.3% yield of diphenylformamide.

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

Procedure: A mixture of 2-(3-iodobenzoyl)acetonitrile (36.2 g, 133.5 mmol) and N,N-diphenylformamide (26.2 g, 133.5 mmol) in toluene (200 ml) was heated at reflux under a nitrogen atmosphere. After 8 h, the reaction mixture was cooled to room temperature and diluted with ether (200 ml) to give 2-(3-iodobenzoyl)-3-phenylaminoacrylonitrile (31.2 g) as a solid. was heated at reflux under a nitrogen atmosphere

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

Procedure: To a solution of N,N-diphenylformamide (19.7 g, 0.10 mol) in 100 ml of chloroform was added 22.8 g (0.11 mol) of phosphorus pentachloride in small portions. After the addition was completed the solution was refluxed for 1 hr. Ethyl 4-aminobenzoate (16.5 g, 0.10 mol) was added in small portions and the solution was refluxed 1 hr. The solution was poured into 100 ml of water and neutralized with concentrated ammonium hydroxide. The chloroform phase was separated, dried (MgSO4), filtered and concentrated to yield a yellow oil. Purification by chromatography using silica gel/benzene yielded the desired product. ##STR11## After the addition was refluxed for 1 hr the solution was refluxed 1 hr The chloroform phase was separated dried (MgSO4) filtered concentrated to yield a yellow oil Purification by chromatography

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

Procedure: To a solution of N,N-diphenylformamide (19.7 g, 0.10 mol) in 100 ml of chloroform was added 22.8 g (0.11 mol) of phosphorus pentachloride in small portions. After the addition was completed the solution was refluxed for 1 hr. Ethyl 4-aminobenzoate (16.5 g, 0.10 mol) was added in small portions and the solution was refluxed 1 hr. The solution was poured into 100 ml of water and neutralized with concentrated ammonium hydroxide. The chloroform phase was separated, dried (MgSO4), filtered and concentrated to yield a yellow oil. Purification by chromatography using silica gel/benzene yielded the desired product. ##STR11## After the addition was refluxed for 1 hr the solution was refluxed 1 hr The chloroform phase was separated dried (MgSO4) filtered concentrated to yield a yellow oil Purification by chromatography

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

Procedure: By essentially the procedure of Example 1, a tube was charged with 40 g of methyldiphenylamine and 2.0 g CuCl2. 2H2O. The reaction was run at 115°-125° C. for 2 hr at 290-400 psi. About 0.1 mole of oxygen was injected incrementally. GC/MS analysis showed a 98.6% conversion of methyldiphenylamine and a 43.3% yield of diphenylformamide.