Water → HCID 4155502, compound

HRID 624551Notes

Reaction equation

HRID 624551 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[N-:9]=[N+:10]=[N-:11].[Na+].O>CS(C)=O>[N:9]([C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8])=[N+:10]=[N-:11]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 27970793-Bromothiophene-2-carboxaldehyde

Product 1

HCID 4155502HCID 4155502, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

3-Bromothiophene-2-carbaldehyde (1) (2000 mg, 10.47 mmol) was treated with sodium azide (1994 mg, 30.7 mmol) in DMSO (27 ml). The reaction was heated to 65° C. for 48 h in a sealed 40 mL vial. The reaction mixture was then taken up into H2O (35 mL) and extracted with diethyl ether (3×20 mL). The organic product layer was washed with 25 ml of saturated NaCl solution, dried over Na2SO4, and concentrated in vacuo to give 3-azidothiophene-2-carbaldehyde (1.22 g, 76% yield).

Workup

  1. extractionextracted with diethyl ether (3×20 mL)
  2. washThe organic product layer was washed with 25 ml of saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40eaa0e223ba48bba6d8d2c367e191b3
Source dataset
uspto-grants-2016_04
Patent number
US09303042B2

Reaction notes

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