Sodium Iodide → 2-(Azidomethyl)-1,3-benzoxazole

HRID 1378721Notes

Reaction equation

HRID 1378721 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])=O.[I-].[Na+].[N-:15]=[N+:16]=[N-:17].[Na+]>CS(C)=O>[N:15]([CH2:2][C:3]1[O:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=1)=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 3505672-chloro-N-(2-hydroxyphenyl)acetamide

Product 1

HCID 229128932-(Azidomethyl)-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 8.34 g (49.8 mmol) of 2-chloro-N-(2-hydroxyphenyl)acetamide (PREPARATION 4) and 0.75 g (5 mmol) of sodium iodide in 25 ml of DMSO were added 3.56 g (5.47 mmol) of sodium azide. A moderate exotherm ensued. After stirring for 30 min the reaction was partitioned between ethyl ether and saline. The organic layers were dried over magnesium sulfate and concentrated. The crude product was chromatographed on silica gel (700 ml) eluting with ethyl acetate/hexane (5/95), the appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 4.60, 7.39, 7.56, 7.76 δ.

Workup

  1. customwas partitioned between ethyl ether and saline
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel (700 ml)
  5. washeluting with ethyl acetate/hexane (5/95)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2d88431576c94fa38d07195b15ce71d2
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

Loading…