Cefonicid → Benzathine

Participants

Reaction Steps

To a stirred solution of cefonicid (5.76 g, 9.8 mmol) in water (6.3% w/w), at pH 5-6 and ambient temperature, methanol (50 ml) was added, followed by a suspension of N,N-dibenzylethylene diamine diacetate (8.6 g, 24 mmol) in methanol (50 ml). The reaction mixture was stirred for 3 h at 20°-25° C., resulting in formation of a white solid. The reaction mixture was cooled to 10°-15° C. and filtered. The white solid was washed with water (3×15 ml) and methanol (3×10 ml). The solid was dried at 30°-35° C. under vacuum. (7.63 g, 99.4% yield). The melting range of the crystals was 191°-193° C. Washed salt with water (50 ml×2) followed by methanol (120 ml) to yield a product with a melting range of 195°-198° C. Elemental Analysis (C34H38N8 O8S3) calcd: C, 52.16; H, 4.89; N, 14.31; S, 12.26. found: C, 52.06; H, 4.89; N, 14.01; S, 12.27.

Provenance & Evidence