Oxalyl chloride → HCID 178514620, compound

HRID 355234Notes

Reaction equation

HRID 355234 reaction equation
[N:1]([C@H:4]1[CH2:7][C@H:6]([C:8]([OH:10])=O)[CH2:5]1)=[N+:2]=[N-:3].C(Cl)(=O)C([Cl:14])=O>ClCCl.CN(C)C=O>[N:1]([C@H:4]1[CH2:7][C@H:6]([C:8]([Cl:14])=[O:10])[CH2:5]1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 178514622HCID 178514622, compound

Product 1

HCID 178514620HCID 178514620, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of trans 3-azidocyclobutanecarboxylic acid (0.58 g, 4.1 mmol) in dichloromethane (10 ml) was added oxalyl chloride (0.45 ml) followed by one drop of N,N-dimethylformamide. The reaction mixture was stirred at 23° C. until the evolution of gas ceased (~2 h) and the solvent was evaporated in vacuo leaving a slightly yellow oil; 0.63 g, 95%; ir (neat) νmax : 2100 (N3) and 1785 cm-1 (C--O of acyl chloride); 1Hmr (CDCl3) δ: 4.12 (1H, m, H-1), 3.6 (1H, m, H-3) and 3.1-2.1 ppm (4H, H-2, H-4).

Workup

  1. custom(~2 h)
  2. customthe solvent was evaporated in vacuo
  3. customleaving a slightly yellow oil

Sources & evidence

ORD record
ord-95f23d5155734d1dbc67dee62be7cd47
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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