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

HRID 857696Notes

Reaction equation

HRID 857696 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) δ 8.74 (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-16570dedb5b94b0898fc0964589b0261
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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