2,4,5-Trichloronitrobenzene → 2-Methyl-4[4,5-dichloro-2-nitroanilino]-1,2,3-triazole-5-carbonitrile

HRID 1388255Notes

Reaction equation

HRID 1388255 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[N:5][N:4]([CH3:9])[N:3]=1.[H-].[Na+].Cl[C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([Cl:20])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]>O1CCCC1>[CH3:9][N:4]1[N:3]=[C:2]([NH:1][C:13]2[CH:18]=[C:17]([Cl:19])[C:16]([Cl:20])=[CH:15][C:14]=2[N+:21]([O-:23])=[O:22])[C:6]([C:7]#[N:8])=[N:5]1

Participants

5

Reactant 3

HCID 69832,4,5-TrichloronitrobenzeneHCID 24758Sodium hydrideHCID 122084054-Amino-2-methyl-1,2,3-triazole-5-carbonitrile

Product 1

HCID 130228262-Methyl-4[4,5-dichloro-2-nitroanilino]-1,2,3-triazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-2-methyl-1,2,3-triazole-5-carbonitrile (1.7 g) in tetrahydrofuran (40 ml) under nitrogen was added sodium hydride (1.0 g, 50% oil dispersion) at room temperature. After 15 minutes, 2,4,5-trichloronitro-benzene (3.13 g) was added to the mixture, which was stirred for six hours under nitrogen. The deep-red solution was then quenched in ice/water/HCl and filtered to leave a yellow-orange solid. The solid was chromatographed on a magnesium silicate column using dichloromethane. The purified product was recrystallised from ethanol to give an orange crystalline solid, melting point 148°-150° C.

Workup

  1. customThe deep-red solution was then quenched in ice/water/HCl
  2. filtrationfiltered
  3. customto leave a yellow-orange solid
  4. customThe solid was chromatographed on a magnesium silicate column
  5. customThe purified product was recrystallised from ethanol
  6. customto give an orange crystalline solid, melting point 148°-150° C.

Sources & evidence

ORD record
ord-abb859f033a645acb5753dcca0b5b04f
Source dataset
uspto-grants-1984_02
Patent number
US04431589

Reaction notes

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