Synthesis
General/Typical Procedure: Preparation of N-2-bromobenzoylglycine: Glycine (0.948 g, 12.628 mmol) was dissolved in water (50 mL), and then dissolved in an aqueous solution of 2-bromobenzoyl chloride (0.649 g, 2.957 mmol). NaOH solution (0.380 g, 9.500 mmol) was added to this solution in portions to maintain a slightly alkaline pH of the mixture. After each addition, the mixture was vigorously stirred. Crushed ice was added to the solution, followed by dropwise addition of concentrated HCl until the mixture was acidified (pH 2-3).
The mixture was then cooled in a refrigerator, filtered, and the precipitate was washed several times with water to remove excess glycine. It was then dried under vacuum to give N-2-bromobenzoylglycine as a white crystalline solid (yield 0.565 g, 74%). Preparation of N-2-iodobenzoylglycine: As with N-2-bromobenzoylglycine, glycine (2.431 g, 32.383 mmol), iodobenzoyl chloride (2.157 g, 8.950 mmol), and NaOH (0.712 g, 17.800 mmol) were reacted to give N-2-iodobenzoylglycine as a white crystalline solid (yield 1.531 g, 62%).
Definition
ChEBI: 2-iodohippuric acid is a member of the class of benzamides resulting from the formal condensation of the carboxy group of 2-iodobenzoic acid with the amino group of glycine. It is a N-acylglycine, an organoiodine compound and a member of benzamides. It is a conjugate acid of a 2-iodohippurate.
