Ammonium Hydroxide → HCID 86746598, compound

Participants

Reaction Steps

2,3-Dihydroxypropylamine (12.10 g, 0.0133 mole) in DMA (10 ml) was added to an ice-cold solution of 3,5-bis-diacetylamino-2,4,6-triiodobenzoyl chloride (29) (35.83 g, 0.05 mole) in DMA (50 ml), with stirring, for 10 min. The reaction mixture was stirred at room temperature, and let stir for 5 hours. Concentrated ammonium hydroxide (30 ml) was added. After 30 min, all solvents were removed in vacuo at 60° C. To the residue, 1N hydrochloric acid (50 ml) was added and the solvent removed in vacuo. The residue was mixed with ice cold water (150 ml) and the precipitate was filtered, washed with water and dried to obtain the product, N-(2',3'-dihydroxypropyl) 2,5-bis-acetylamino-2,4,6-triiodobenzamide (30), as a white solid in high yield. TLC: (silica gel): 0.36 in CHCl3 /MeOH 8:2. NMR: (DMSO-d6): COCH3 (2.02, singlet, 6H); (--CH2 -- and --CH protons (3.05 to 3.85, broad multiplet, 5H); --OH (4.2, singlet); ArCOHN-(8.4 to 8.7, broad triplet, 1H); Ar--NHCO-- (9.85 to 10.15, broad doublet, 2H).

Provenance & Evidence