Chloroform → 4-(3-Azidopropoxy)-pyridine-2,6-dicarbonyldichloride

HRID 411871Notes

Reaction equation

HRID 411871 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([C:14]([OH:16])=O)[N:11]=C(C(O)=O)[CH:9]=1)=[N+:2]=[N-:3].[C:20](Cl)(=O)[C:21]([Cl:23])=[O:22].C(Cl)(Cl)[Cl:27]>CN(C=O)C>[N:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([C:14]([Cl:27])=[O:16])[N:11]=[C:20]([C:21]([Cl:23])=[O:22])[CH:9]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 65578Oxalyl chlorideHCID 223236464-(3-Azidopropoxy)-pyridine-2,6-dicarboxylic acid

Product 1

HCID 867556824-(3-Azidopropoxy)-pyridine-2,6-dicarbonyldichloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-azidopropoxy)-pyridine-2,6-dicarboxylic acid 43 (1.33 g, 5.0 mmol) was suspended in chloroform (80 mL) and DMF (0.4 mL). Oxalyl chloride (2.7 mL, 3.9 g, 30.7 mmol) was added dropwise to the above stirred suspension. The resulting reaction mixture was stirred at room temperature for 2 days. The solvent was evaporated and the residue was dried under high vacuum for 24 hours. The 4-(3-azidopropoxy)-pyridine-2,6-dicarbonyldichloride obtained was used for the next coupling reaction directly without further purification.

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was evaporated
  3. customthe residue was dried under high vacuum for 24 hours

Sources & evidence

ORD record
ord-0afe35d4b2df4bb7afc45ea63cb92b71
Source dataset
uspto-grants-2003_05
Patent number
US06559303B1

Reaction notes

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