Dimethylformamide → HCID 54273058, compound

Reaction equation

[N:1]([CH:4]([CH2:8][CH2:9][CH3:10])[C:5](O)=[O:6])=[N+:2]=[N-:3].C(Cl)(=O)C([Cl:14])=O.CN(C)C=O>ClCCl>[N:1]([CH:4]([CH2:8][CH2:9][CH3:10])[C:5]([Cl:14])=[O:6])=[N+:2]=[N-:3]

Participants

Procedure

A solution of (2R and 2S) 2-azidopentanoic acid (2.213 g, 15.46 mmol) in dry dichloromethane (20 ml) was treated with oxalyl chloride (1.57 ml, 18.55 mmol) and a drop of N,N-dimethyl formamide. After the evolution of gas had ceased (2 h), the solvent was evaporated under reduced pressure and the residual liquid was distilled off (bulb to bulb) under vacuum to give 2.224 g (89%) of a clear oil: bp 50°-55° C./5 torr (air bath temperature); ir (film) νmax : 2105 (N3), 1785 cm-1 (C=O); 1Hmr (CDCl3) δ: 4.1 (1H, dd, J=7, J=6, H-2), 2.2-1.2 (4H, m, H-3 and H-4), and 0.98 ppm (3H, distorted t, J=6, H-5).