Water → HCID 14624362, compound

HRID 1031130Notes

Reaction equation

HRID 1031130 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-])=O)[C:3]=1[N:15]1[C:19]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[N:18][C:17]([C:25]([CH3:28])([CH3:27])[CH3:26])=[N:16]1.O.[OH-].[Na+]>CO.Cl>[NH2:12][C:4]1[CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:15]1[C:19]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[N:18][C:17]([C:25]([CH3:27])([CH3:26])[CH3:28])=[N:16]1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14624357HCID 14624357, compound

Product 1

HCID 14624362HCID 14624362, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1-(2-Chloro-6-nitro-4-trifluoromethylphenyl)-3-tertiary-butyl-5-diethylamino-1,2,4-triazole (0.6g) was dissolved in methanol (20ml) and the solution warmed to 50° C. A solution of stannous chloride dihydrate (2.3g) in concentrated hydrochloric acid (20ml) was added with vigorous stirring. The reaction mixture was allowed to cool, then stirred at room temperature for 30 minutes and poured into water. The solution was basified to pH 8 with 2N sodium hydroxide solution, and then extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulphate and the solvent evaporated under reduced pressure to afford a pale yellow oil which crystallised on standing. Recrystallisation from hexane gave 1-(2-amino-6-chloro-4-trifluoromethylphenyl)-3-tertiary-butyl-5-diethylamino-1,2,4-triazole (260mg).

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent evaporated under reduced pressure
  6. customto afford a pale yellow oil which
  7. customcrystallised
  8. customRecrystallisation from hexane

Sources & evidence

ORD record
ord-9d423fb5e43b40f792efdce289bc4abd
Source dataset
uspto-grants-1992_04
Patent number
US05109004

Reaction notes

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