Sodium hydride → HCID 13022825, compound

HRID 1388252Notes

Reaction equation

HRID 1388252 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[N:5][N:4]([CH3:9])[N:3]=1.[H-].[Na+].F[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21]>O1CCCC1>[CH3:9][N:4]1[N:3]=[C:2]([NH:1][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[N+:20]([O-:22])=[O:21])[C:6]([C:7]#[N:8])=[N:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 677672,5-DifluoronitrobenzeneHCID 122084054-Amino-2-methyl-1,2,3-triazole-5-carbonitrile

Product 1

HCID 13022825HCID 13022825, compound

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 (35 ml) under nitrogen, was added sodium hydride (1.0 g; 50% oil dispersion) at room temperature. After 15 minutes, 2,5-difluoronitrobenzene (2.22 g) was added to the mixture, which was stirred overnight under nitrogen. The deep red solution was then quenched in ice/water/HCl and filtered to give an orange solid. The solid was chromatographed on a magnesium silicate column using dichloromethane; the purified product recrystallised from ethyl acetate-ethanol to give an orange crystalline solid, melting point 159°-160° C.

Workup

  1. customThe deep red solution was then quenched in ice/water/HCl
  2. filtrationfiltered
  3. customto give an orange solid
  4. customThe solid was chromatographed on a magnesium silicate column
  5. customthe purified product recrystallised from ethyl acetate-ethanol
  6. customto give an orange crystalline solid, melting point 159°-160° C.

Sources & evidence

ORD record
ord-0ad30b5d085e444dae04289f9d485fa5
Source dataset
uspto-grants-1984_02
Patent number
US04431589

Reaction notes

Loading…