Dimethylformamide → 6-(Azidomethyl)benzoxazole

HRID 1685073Notes

Reaction equation

HRID 1685073 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7](C)[O:8][C:4]=2[CH:3]=1.C[N:13]([CH:15]=O)C.[N-:17]=[N+:18]=[N-].[Na+]>O>[N:13]([CH2:15][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[CH:7][O:8][C:4]=2[CH:3]=1)=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 100360776-Bromo-2-methylbenzo[d]oxazole

Product 1

HCID 586863016-(Azidomethyl)benzoxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 ml flask was loaded with 6-bromo-methyl-benzooxazole (1.8 g, 8.5 mmole), 40 ml DMF and sodium azide (1.1 g, 16.98 mmole). The reaction mixture was stirred at room temperature, overnight. The reaction mixture was diluted with 40 ml water and extracted 2×50 ml EtOAc. Combined organic layers were washed with water, brine, dried over sodium sulfate, filtered and concentrated to afford 2 g oily crude. HNMR shows 90% pure product. This was used for next step.

Workup

  1. extractionextracted 2×50 ml EtOAc
  2. washCombined organic layers were washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford 2 g oily crude

Sources & evidence

ORD record
ord-7acdacfb8c8d42a294def26c65fbc909
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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