1H-1,2,4-Triazole → 1-(3-Methyl-4-nitrophenyl)-1,2,4-triazole

HRID 2231660Notes

Reaction equation

HRID 2231660 reaction equation
F[C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.[NH:12]1[CH:16]=[N:15][CH:14]=[N:13]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:11][C:4]1[CH:3]=[C:2]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 10340Sodium CarbonateHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 144502481-(3-Methyl-4-nitrophenyl)-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-fluoro-6-nitrotoluene (50.0 g), 1,2,4-triazole (22.2 g) and sodium carbonate (34.0 g) was heated with stirring in dimethylformamide (300 cm3) at 130° for 16 hours. The cooled mixture was then concentrated in vacuo, the residue was acidified to pH1 with 4M hydrochloric acid, and the resulting solution was extracted with chloroform (2×25 cm3) to remove any neutral material. The combined aqueous phases were basified to pH10 with 2.5M sodium hydroxide solution and the mixture was extracted with chloroform (3×250 cm3). The combined and dried (MgSO4) organic extracts were concentrated in vacuo to give a solid which was recrystallised from toluene to give 1-(3-methyl-4-nitrophenyl)-1,2,4-triazole, m.p. 116°-7°.

Workup

  1. temperaturewas heated
  2. concentrationThe cooled mixture was then concentrated in vacuo
  3. extractionthe resulting solution was extracted with chloroform (2×25 cm3)
  4. customto remove any neutral material
  5. extractionthe mixture was extracted with chloroform (3×250 cm3)
  6. dry with materialdried (MgSO4) organic extracts
  7. concentrationwere concentrated in vacuo
  8. customto give a solid which
  9. customwas recrystallised from toluene

Sources & evidence

ORD record
ord-3cab3f00de644381bf7b8a7b4131371b
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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