4-Chloro-3-nitrotoluene → HCID 178427279, compound

HRID 883901Notes

Reaction equation

HRID 883901 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-])=O.[NH:12]1[CH:16]=[N:15][C:14]([SH:17])=[N:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([S:17][C:14]2[N:15]=[CH:16][NH:12][N:13]=2)=[C:3]([NH2:9])[CH:4]=1

Participants

6

Reactant 3

HCID 69764-Chloro-3-nitrotolueneHCID 11430Potassium CarbonateHCID 178527894HCID 178527894, compound

Product 1

HCID 178427279HCID 178427279, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 1-Chloro-4-methyl-2-nitro-benzene (3.00 g, 17.5 mmol), 1H-[1,2,4]Triazole-3-thiol (1.94 g, 19.2 mmol), and K2CO3 (4.22 g, 30.6 mmol) heated in DMF at 100° C. for 16 hrs. Reaction mixture was then cooled to room temperature and diluted with water and extracted with ethyl acetate. Dried over Na2SO4, filtered and concentrated under vacuum giving the title compound (1.1 g, 26%).

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialDried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3678162b721b412ba0623619a577ebf9
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

Loading…