Oxalyl chloride → HCID 178514619, compound

HRID 355238Notes

Reaction equation

HRID 355238 reaction equation
[C:1]([C@@H:4]1[CH2:7][C@H:6]([N:8]=[N+:9]=[N-:10])[CH2:5]1)(O)=[O:2].C(Cl)(=O)C([Cl:14])=O>ClCCl.CN(C)C=O>[N:8]([C@@H:6]1[CH2:7][C@H:4]([C:1]([Cl:14])=[O:2])[CH2:5]1)=[N+:9]=[N-:10]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 178514621HCID 178514621, compound

Product 1

HCID 178514619HCID 178514619, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of cis-3-carboxycyclobutyl azide (1.86 g, 13.2 mmol) in dichloromethane (30 ml) was treated with oxalyl chloride (1.5 ml, 17.2 mmol) followed by one drop of N,N-dimethylformamide. The reaction mixture was stirred at 23° C. until the evolution of gas ceased (0.5-1 h) and the solvent was evaporated in vacuo leaving a yellow oil; 2.0 g, 95% ir (neat) νmax :2100 (N3) and 1785 cm-1 (C=O of acylchloride).

Workup

  1. custom(0.5-1 h)
  2. customthe solvent was evaporated in vacuo
  3. customleaving a yellow oil

Sources & evidence

ORD record
ord-10dc1ee90c8f444e99afccbc8db1d197
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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