5-(4-Chlorophenyl)-2-furaldehyde → HCID 70098637, compound

Participants

Reaction Steps

A mixture of 1-phenylmethyleneamino-3-[2-(dimethylamino)ethyl]-2-imidazolidinone, prepared as described in Part II above (6.17 g, 0.023 mole) in 2N HCl (166 ml) is treated with 5% palladium on carbon (50% wet catalyst) (1.3 g). The reaction mixture is reduced on Parr apparatus under hydrogen. The hydrogen uptake stopped after 1/2 hour with 100% of theoretical uptake observed. The catalyst is removed and the filtrate concentrated under reduced pressure to leave a white residue. The residue is treated with a solution of 5-(4-chlorophenyl)-2-furancarboxaldehyde (prepared as described in U.S. Pat. No. 4,882,354 to Huang et al., assigned to Norwich Eaton Pharmaceuticals, Inc., issued Nov. 21, 1989, see Example 3, cols. 7, 8, hereby incorporated by reference herein) (4.81 g, 0.023 mole) in dry dimethylformamide (137 ml). The reaction is stirred at ambient temperature overnight. The reaction mixture is filtered and washed with anhydrous ether to give 1-[[[5-(4-chlorophenyl)-2-furanyl]methylene]amino]-3-[2-(dimethylamino) ethyl]-2-imidazolidinone hydrochloride.

Provenance & Evidence