Oxalyl chloride → HCID 20505495, compound

HRID 355250Notes

Reaction equation

HRID 355250 reaction equation
[N:1]([CH:4]([CH2:8][CH2:9][C:10]#[N:11])[C:5](O)=[O:6])=[N+:2]=[N-:3].C(Cl)(=O)C([Cl:15])=O>C(Cl)Cl.CN(C=O)C>[N:1]([CH:4]([CH2:8][CH2:9][C:10]#[N:11])[C:5]([Cl:15])=[O:6])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 20505467HCID 20505467, compound

Product 1

HCID 20505495HCID 20505495, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-azido-4-cyanobutyric acid (0.76 g, 4.94 mmol) in dry methylene chloride (20 ml) was added oxalyl chloride (0.65 g, 5.1 mmol) and a drop (~15 mg) of DMF. The reaction mixture was stirred at room temperature until the evolution of gas ceased (15 min) and then refluxed for 10 min. Removal of the solvent in vacuo gave 0.84 g (99%) of the title compound as a syrup; ir (neat) νmax : 2250, 2110, 1780 cm-1.

Workup

  1. custom(15 min)
  2. temperaturerefluxed for 10 min
  3. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-8d696241dc9e4f54bf6d64b13860d52d
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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