Ethyl Acetate → 4-(2-Azidomethyl-phenyl)-[1,2,3]thiadiazole

HRID 397497Notes

Reaction equation

HRID 397497 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[N:11][S:12][CH:13]=1.[N-:14]=[N+:15]=[N-:16].[Na+].C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C>CN(C)C=O>[N:14]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[N:11][S:12][CH:13]=1)=[N+:15]=[N-:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 21226206Ethyl acetate hexaneHCID 218662434-(2-Bromomethyl-phenyl)-[1,2,3]thiadiazole

Product 1

HCID 218662814-(2-Azidomethyl-phenyl)-[1,2,3]thiadiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(2-bromomethyl-phenyl)-[1,2,3]thiadiazole (7.0 g, 0.027 mol) and sodium azide (5.3 g, 0.081 mol) in N,N-dimethylformamide (200 ml) was stirred at room temperature overnight. Ethyl acetate was added and the reaction mixture was washed with water and brine. Drying and solvent evaporation gave an oil; flash chromatography (silica gel, hexane-ethyl acetate, 96:4) gave 4-(2-azidomethyl-phenyl)-[1,2,3]thiadiazole; 1H NMR (CDCl3, 300 MHz) δ8.74 (s, 1H), 7.76 (m, 1H), 7.53 (m, 3H), 4.54 (s, 2H).

Workup

  1. washthe reaction mixture was washed with water and brine
  2. customDrying
  3. customsolvent evaporation
  4. customgave an oil

Sources & evidence

ORD record
ord-037756aa0ef6463a8baae3eda02eb1ad
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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