Sodium Azide → HCID 59409876, compound

HRID 2066818Notes

Reaction equation

HRID 2066818 reaction equation
Cl[CH2:2][C:3]1([CH3:16])[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)[CH2:4]1.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C)C=O.O>[N:17]([CH2:2][C:3]1([CH3:16])[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)[CH2:4]1)=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 59409862HCID 59409862, compound2×

Product 1

HCID 59409876HCID 59409876, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(chloromethyl)-3-(5-chloropyridin-2-yl)-5-methyl-1,3-oxazolidin-2-one (1.01 g, INTERMEDIATE 17) and sodium azide (503 mg) was heated to 140° C. in 40 ml of dimethylformamide for 40 h. The mixture was then cooled to room temperature, and diluted with 150 ml of water and extracted with 150 ml of ethyl acetate (3×). The combined organic layers were washed with water (100 ml) and brine (100 ml). Then they were dried over sodium sulfate and concentrated in vacuo (overnight to remove dimethylformamide) to provide 570 mg (55%) of the title compound. Mass spectrum (ESI) 268.1 (M+1).

Workup

  1. extractionextracted with 150 ml of ethyl acetate (3×)
  2. washThe combined organic layers were washed with water (100 ml) and brine (100 ml)
  3. dry with materialThen they were dried over sodium sulfate
  4. concentrationconcentrated in vacuo (overnight to remove dimethylformamide)

Sources & evidence

ORD record
ord-1a35ebe8adce460da8d3a352c8e4afc7
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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