Chlorosuccinimide → HCID 86644167, compound
Reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][C@:5]([CH3:10])([CH:7]=[N:8][OH:9])[CH2:4][O:3]1.[Cl:12]N1C(=O)CCC1=O>CN(C=O)C.O>[OH:9][N:8]=[C:7]([Cl:12])[C@:5]1([CH3:10])[CH2:4][O:3][C:2]([CH3:11])([CH3:1])[O:6]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
(R)-2,2,4-Trimethyl-1,3-dioxolane-4-carbaldehyde oxime (4.8 g, 30 mmol) was dissolved in DMF (100 mL) and 1-chloropyrrolidine-2,5-dione (4.0 g, 30 mmol) was added. The reaction was stirred at ambient temperature overnight, then poured in water (600 mL) with of stirring. After 15 minutes the cloudy suspension was extracted with EtOAc and washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated, to afford (S)-N-hydroxy-2,2,4-trimethyl-1,3-dioxolane-4-carbimidoyl chloride (5.5 g, 28 mmol, 94% yield).