Sodium Hydroxide → HCID 178459270, compound

Participants

Reaction Steps

NaOH (0.8 g) was dissolved in water (20 mL) and then cooled to room temperature. 1,1-dimethylbiguanide hydrochloride (3.6 g) was then added and stirred to obtain a clear solution. The resulting solution was added to a suspension of {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid (UD1) (9.1 g) in ethanol (80 mL) with stirring at room temperature. The reaction mixture turned clear in 3-5 minutes. The volatiles were evaporated to obtain a syrup, which was dissolved in ethanol (100 mL) and then concentrated. White precipitate was obtained when about 50 mL of volatiles were removed by evaporation. This precipitate was filtered and dried under reduced pressure to obtain a 1,1-dimethylbiguanide salt of {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid. The 1H NMR spectrum recorded in DMSO-d6 indicated the precipitate contained {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid and 1,1-dimethylbiguanide in 1:1 ratio. 1H NMR (400 MHz, DMSO-d6): δ 0.85 (t, 3H), 1.05-2.15 (m, 20H), 2.92 (s, 6H), 3.18 (m, 1H), 3.30 (s, 2H), 3.34 (t, 2H), 3.45 (br, 1H), 7.1 (br, NH protons), 7.21 (s, 1H) ppm.

Provenance & Evidence