N-Phenyl-o-phenylenediamine → HCID 69528975, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.48 g (8.15 mmoles) of (S)-2-amino-4-butyrolactone hydrobromide and 3.12 ml (17.9 mmoles) of diisopropylethylamine in 80 ml of anhydrous CH2Cl2 is added slowly (4 hours) into a three-necked flask containing a solution of 0.89 g (3 mmoles) of triphosgene in 45 ml of anhydrous CH2Cl2, under an inert atmosphere. After stirring for a further 15 minutes, a solution of 1.5 g (8.15 mmoles) of N1-phenyl-1,2-benzenediamine and 3.12 ml (17.9 mmoles) of diisopropylethylamine in 45 ml of anhydrous CH2Cl2 is added in one go. The reaction mixture is then heated for 5 hours at 60° C. After concentration to dryness under vacuum, the residue is divided between 50 ml of AcOEt and 50 ml of water. After stirring and decanting, the organic phase is washed successively with 50 ml of water and 50 ml of salt water. The organic solution is then dried over Na2SO4, filtered and concentrated under vacuum. The evaporation residue is then purified on a silica column (eluent: Heptane/AcOEt: 1/2). Pink solid.

Provenance & Evidence