Dimethylformamide → trans 2-Azidomethyl-1-cyclopropanecarboxylic acid chloride

HRID 1680340Notes

Reaction equation

HRID 1680340 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:7][C@H:6]1[C:8]([OH:10])=O)=[N+:2]=[N-:3].C(Cl)(=O)C([Cl:14])=O.CN(C)C=O>ClCCl>[N:1]([CH2:4][C@@H:5]1[CH2:7][C@H:6]1[C:8]([Cl:14])=[O:10])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 53661350(1R,2R)-2-(Azidomethyl)cyclopropane-1-carboxylic acid

Product 1

HCID 53734291trans 2-Azidomethyl-1-cyclopropanecarboxylic acid chlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of trans-2-azidomethyl-1-cyclopropane carboxylic acid (2.188 g, 15.50 mmol) in dry dichloromethane (25 ml) was treated at room temperature with oxalyl chloride (1.57 ml, 18.60 mmol) and a drop of N,N-dimethylformamide. After the evolution of gas has ceased (2.5 h), the solvent was evaporated under reduced pressure and the residue was distilled under vacuum (bulb to bulb distillation) to give 2.411 g (98%) of a clear oil: bp 70°-75° C./0.8 mm Hg (air bath temperature); ir (film) νmax : 2100 (N3), 1775 cm-1 (C=O); 1Hmr (CDCl3) δ: 3.33 (2H, d, J=6, CH2N3) ~2.2 - 1.0 ppm (4H, m, cyclopropyl).

Workup

  1. custom(2.5 h)
  2. customthe solvent was evaporated under reduced pressure
  3. distillationthe residue was distilled under vacuum (bulb to bulb distillation)

Sources & evidence

ORD record
ord-d7336dc0f4404d8b8535068ab999f5bd
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

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