Dimethyl Sulfoxide → Methyl 6-(azidomethyl)nicotinate

HRID 2355284Notes

Reaction equation

HRID 2355284 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Cl)=[N:6][CH:5]=1.CS(C)=O.[N-:17]=[N+:18]=[N-:19].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:17]=[N+:18]=[N-:19])=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10340Sodium CarbonateHCID 33557Sodium AzideHCID 15331516Methyl 6-(chloromethyl)nicotinate

Product 1

HCID 22565575Methyl 6-(azidomethyl)nicotinateYield 86.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Add 6-chloromethyl-nicotinic acid methyl ester (9.1 g, 40.98 mmol) and dimethylsulfoxide (100 mL) into a flask and cool to 0° C. Add sodium azide (4 g, 61.47 mmol) and sodium carbonate (13 g, 122.9 mmol) to the reaction mixture. Let the mixture slowly warm to room temperature. Stir for 1 hr at room temperature. Add water (100 mL) to the mixture. Extract with diethyl ether (100 mL×3). Wash the organic layer with water and brine. Dry with sodium sulfate. Remove solvent under reduced pressure to give the product (6.8 g, 86% yield) as light yellow oil. MS (m/z): 193.3 (M+1).

Workup

  1. temperatureslowly warm to room temperature
  2. extractionExtract with diethyl ether (100 mL×3)
  3. washWash the organic layer with water and brine
  4. dry with materialDry with sodium sulfate

Sources & evidence

ORD record
ord-0d64b82baf994e52b9ffb87f736bf578
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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