Oxalyl chloride → HCID 20505480, compound

HRID 1680369Notes

Reaction equation

HRID 1680369 reaction equation
[N:1]([CH:4]([CH2:9][CH3:10])[CH2:5][C:6](O)=[O:7])=[N+:2]=[N-:3].C(Cl)(=O)C([Cl:14])=O>CN(C=O)C>[N:1]([CH:4]([CH2:9][CH3:10])[CH2:5][C:6]([Cl:14])=[O:7])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 20505517HCID 20505517, compound

Product 1

HCID 20505480HCID 20505480, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

3-Azidopentanoic acid (1.72 g, 12.2 mmol) was dissolved in oxalyl chloride (1.49 ml, 2.22 g, 17.5 mmol) and to this stirring solution was added one drop of DMF. The mixture was stirred at room temperature for 30 min and heated at 80° C. for 40 min. The residue was distilled under vacuum, bp 33° C. (0.1 mm), to give a colorless oil (936 mg, 48.2%); ir (neat) νmax : 2100 (N3), and 1795 cm-1 (C=O of acid chloride); 1Hmr (CDCl3) δ: 1.03 (3H, t), 1.60 (2H, m), 3.03 (2H, d) and 3.80 ppm (H, m). Anal. calcd for C5H8N3Cl: C 37.16, H 4.99; found: C 37.40, H 4.92.

Workup

  1. temperatureheated at 80° C. for 40 min
  2. distillationThe residue was distilled under vacuum, bp 33° C. (0.1 mm)

Sources & evidence

ORD record
ord-3af25e77f57c434586cfbecad4fd786e
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

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