Sodium Azide → HCID 59409897, compound

HRID 2066802Notes

Reaction equation

HRID 2066802 reaction equation
Cl[CH2:2][CH:3]1[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-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O.O>[N:16]([CH2:2][CH:3]1[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]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 594099115-(Chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one2×

Product 1

HCID 59409897HCID 59409897, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one (204 mg, INTERMEDIATE 1) and sodium azide (107 mg) was heated to 100° C. in 10 ml of dimethylformamide for 15 h. The sample was then diluted with 100 ml of water and extracted with 100 ml of ethyl acetate (3×). The combined organic layers were washed with water (100 ml) and brine (100 ml). They were then dried over sodium sulfate and concentrated in vacuo to provide 139 mg (67%) of the title compound in >95% purity via LC/MS. Mass spectrum (ESI) 254.0 (M+1).

Workup

  1. extractionextracted with 100 ml of ethyl acetate (3×)
  2. washThe combined organic layers were washed with water (100 ml) and brine (100 ml)
  3. dry with materialThey were then dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-335e9f9e97314378bcb1d971f73d9f99
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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