Dimethylformamide → HCID 54273058, compound

HRID 355247Notes

Reaction equation

HRID 355247 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

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 20206318HCID 20206318, compound

Product 1

HCID 54273058HCID 54273058, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. custom(2 h)
  2. customthe solvent was evaporated under reduced pressure
  3. distillationthe residual liquid was distilled off (bulb to bulb) under vacuum

Sources & evidence

ORD record
ord-0018c18d341e4d789be33a445f7b5141
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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