Potassium Carbonate → HCID 21465302, compound

Participants

Reaction Steps

Compound 4 (4.04 g, 0.02 mole) and ethyl 4-methylaminobenzoate hydrochloride (3) (4.10 g, 0.02 mole) were dissolved in 200 ml of tetrahydrofuran. The solution was chilled in an ice bath, and to the solution was added slowly a potassium carbonate solution (3.0 g, 0.022 mole in 200 ml water) with stirring. After 24 hours of continuous stirring at room temperature, a yellow precipitate was collected and washed with water. Recrystallization of the product from methanol gave 2.4 g (70% yield) of yellow solid 5. This solid had a melting point of 206°-207° C. The IR spectrum (KBr) showed absorptions corresponding to --NH2 at 3389.9, 3194, and 3264 cm-1, --C≡N at 2240 cm-1, and --C(=O)O-- at 1713 cm-1. The nmr spectrum (DMSO-d6) revealed signals at 7.75 δ (2H,b,NH2), 7.70 δ (2H,d,arom), 6.67 δ (2H,d,arom), 4.35 δ (2H, s,CH2N--), 4.21 δ (2H,q,OCH2CH3), 3.20 δ (3H,s,NCH3), and 1.32 δ (3H,t,CH2CH3). The FAB mass spectrum showed a molecular ion peak at m/z 345. This peak confirmed that the molecular weight of this compound was 345. Elemental analysis confirmed the presence of C, H, N and Cl in the compound.

Provenance & Evidence