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

HRID 355242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 355242
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f02e638dcc6b4edea9bee768c62ad70e
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04378314

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