Sodium Azide → HCID 22225783, compound

HRID 1745391Notes

Reaction equation

HRID 1745391 reaction equation
Br[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]#[N:9])[N:7]=1.[N-:10]=[N+:11]=[N-:12].[Na+]>CN(C=O)C.O>[N:10]([CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]#[N:9])[N:7]=1)=[N+:11]=[N-:12]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 220327292-(Bromomethyl)-1,3-thiazole-4-carbonitrile

Product 1

HCID 22225783HCID 22225783, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Bromomethyl-thiazole-4-carbonitrile (1.6 g, 7.8 mmol) was dissolved in 20 mL DMF and sodium azide (0.768 g, 11.8 mmol) was added. The reaction was allowed to stir for 16 h at room temperature and then diluted with water (50 mL). The aqueous layer was extracted with ethyl acetate (3×) and the combined organic layers were washed again with 75 ml of brine, dried with anhydrous sodium sulfate and concentrated in vacuo to yield 1.20 g (92%) of the title compound as a gummy material which was used in next step with out further purification.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  2. washthe combined organic layers were washed again with 75 ml of brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71ac20bd6f9a48cbb0dceee81c0556cf
Source dataset
uspto-grants-2006_03
Patent number
US07019019B2

Reaction notes

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