Di-tert-butyl iminodiacetate

• multi-carboxylic acid-containing carbocyanine dyes
• monosubstituted difunctionalized polyhedral oligomeric silsesquioxanes (POSS) monomers
• multigenerational fluorinated dendrimers
• 2,6-dipyrazol-1-ylpyridine derivatives

107-59-5

85916-13-8

The general procedure for the synthesis of di-tert-butyl iminodiacetate from tert-butyl chloroacetate is as follows: in a 250 mL three-necked flask equipped with a thermometer, condenser tube and mechanical stirring device, 120 mL of methanol was added. Under continuous stirring, 120.0 g of tert-butyl chloroacetate (0.8 mol) was heated to 65 °C and 5.1 g of ammonia (0.3 mol) was slowly passed through. The reaction was carried out for 2 hours and then continued to hold the reaction for 5 hours. After the reaction mixture was cooled to room temperature, it was filtered to remove the resulting white solid ammonium chloride. The filtrate was concentrated by rotary evaporation to recover about 110 mL of methanol. The concentrated residue was cooled to 0 °C to induce precipitation of the product. The precipitate was collected by filtration to give 23.3 g of di-tert-butyl iminodiacetate with a melting point of 41 °C.