Dimethylformamide → HCID 70098395, compound

Participants

Reaction Steps

A solution of 4.8 g (0.017 mole) of 3-[3-(dimethylamino) propyl]-1-[(phenylmethylene)amino]-2-imidazolidinone (prepared as described in Part III above) in 125 ml of 2 N HCl is treated with 1 g of 5% Pd/C (50% H20) and placed on the Parr reduction apparatus, with the theoretical amount of H2 being absorbed over a 30 minute period. The catalyst is removed by filtration and the solvent is removed in vacuo. The residual oil is dissolved in 100 ml of dimethylformamide and treated all at once with 3.51 g (0.0170 mole) of 5-(4-chlorophenyl)-2-furancarboxaldehyde (prepared as described in U.S. Pat. No. 4,882,354 to Huang et al., (issued Nov. 21, 1989), assigned to Norwich Eaton Pharmaceuticals, Inc., see Example 3, cols. 7 & 8, hereby incorporated by reference herein) with dissolution. A 1.0 g portion of 3 Angstrom molecular sieves is added and the reaction is stirred 16 to 18 hours at ambient temperature. The resulting mixture is heated to reflux with dimethylformamide being added to dissolution. The molecular sieves are removed by filtration and the solvent is removed in vacuo. The residual semi-solid is crystallized by trituration with ether. The solid is recrystallized from S.D.A. #32, (activated charcoal) and dried in a vacuum pistol over refluxing ethyl acetate to yield 2.7 g of 1-[[[5-(4-chlorophenyl)-2-furanyl]methylene]amino]-3-(3-dimethylaminopropyl)-2-imidazolidinone hydrochloride.

Provenance & Evidence