Chlorosuccinimide → 4-chloro-1-(4-nitrophenyl)-1H-1,2,3-triazole

HRID 40735Notes

Reaction equation

HRID 40735 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([Si](C)(C)C)[N:12]=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C(=O)N([Cl:26])C(=O)C1>CC#N>[Cl:26][C:13]1[N:12]=[N:11][N:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 107066131-(4-nitrophenyl)-4-(trimethylsilyl)-1H-1,2,3-triazole

Product 1

HCID 687732414-chloro-1-(4-nitrophenyl)-1H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1-(4-nitrophenyl)-4-(trimethylsilyl)-1H-1,2,3-triazole (0.5 g, 1.9 mmol) and silica gel (2.9 g) in anhydrous CH3CN (10 mL) was added NCS (1.1 g, 6.7 mmol). The mixture was heated to 80° C. for 24 h. The reaction was cooled, filtered and concentrated in vacuo. The resulting crude residue was purified by chromatography on silica gel (EtOAc/hexanes) to give 4-chloro-1-(4-nitrophenyl)-1H-1,2,3-triazole. 1H NMR (CDCl3, 400 MHz) δ 8.39 (dd, 2H), 8.02 (s, 1H), 7.89 (dd, 2H).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude residue was purified by chromatography on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-49df953b17984f08aaa0398389f1a728
Source dataset
uspto-grants-2013_09
Patent number
US08530480B2

Reaction notes

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