Ammonia → 2-(2,6-dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazole-4-carboxamide

HRID 973677Notes

Reaction equation

HRID 973677 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[N:17]=[C:16]([C:18](O)=[O:19])[CH:15]=[N:14]1.S(Cl)(Cl)=O.[NH3:25]>O1CCCC1>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[N:17]=[C:16]([C:18]([NH2:25])=[O:19])[CH:15]=[N:14]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 541736102-(2,6-dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazole-4-carboxylic acid

Product 1

HCID 199888872-(2,6-dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2,6-Dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazole-4-carboxylic acid (8.18 g) was treated with thionyl chloride (150 ml) to give crude acid chloride. A solution of this in tetrahydrofuran was added to ammonia with ice cooling. The mixture was stirred at room temperature for one hour, solvent was removed and the product extracted with ethyl acetate and worked up in conventional manner to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazole-4-carboxamide, m.p. 239° (Compound 14 ).

Workup

  1. customto give crude acid chloride
  2. customsolvent was removed
  3. extractionthe product extracted with ethyl acetate

Sources & evidence

ORD record
ord-a5034140cafb45e490a34088dab0a5a1
Source dataset
uspto-grants-1991_11
Patent number
US05064844

Reaction notes

Loading…