Water → HCID 21998166, compound

HRID 1977504Notes

Reaction equation

HRID 1977504 reaction equation
N(OC(C)(C)C)=O.[N-:8]=[N+:9]=[N-:10].[Na+].[Cl:12][C:13]1[CH:19]=[C:18]([F:20])[C:17]([C:21]2[C:25]([Cl:26])=[C:24]([C:27]([F:30])([F:29])[F:28])[N:23]([CH3:31])[N:22]=2)=[CH:16][C:14]=1N.O>FC(F)(F)C(O)=O>[Cl:12][C:13]1[CH:19]=[C:18]([F:20])[C:17]([C:21]2[C:25]([Cl:26])=[C:24]([C:27]([F:29])([F:30])[F:28])[N:23]([CH3:31])[N:22]=2)=[CH:16][C:14]=1[N:8]=[N+:9]=[N-:10]

Participants

6

Reactant 4

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 33557Sodium AzideHCID 22491729HCID 22491729, compound

Product 1

HCID 21998166HCID 21998166, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.46 g (4.5 mmol) of tert-butyl nitrite and 0.3 g (4.5 mmol) of sodium azide were added to a solution of 1 g (3 mmol) of 2-chloro-5-(4-chloro-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-4-fluoroaniline in 20 ml of trifluoroacetic acid. The mixture was subsequently stirred for 2 hours and then admixed with 50 ml of water. The resulting product was extracted from the aqueous phase using 100 ml of methyl tert-butyl ether. The extract was washed with 10% strength aqueous sodium hydroxide solution, then dried over magnesium sulfate and finally concentrated. The crude product was purified by silica gel chromatography (eluent: hexane/ethyl acetate=1:1). Yield: 0.7 g; 1H NMR (400 MHz; in (CD3)2SO): δ[ppm]=4.10 (s,3H), 7.53 (d,1H), 7.77 (d,1H).

Workup

  1. extractionThe resulting product was extracted from the aqueous phase
  2. washThe extract was washed with 10% strength aqueous sodium hydroxide solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationfinally concentrated
  5. customThe crude product was purified by silica gel chromatography (eluent: hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ccf812cb2750458492ca5a6cffc7f9b2
Source dataset
uspto-grants-2001_05
Patent number
US06232470B1

Reaction notes

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