Tert-Butyl nitrite → HCID 21188064, compound

HRID 1383616Notes

Reaction equation

HRID 1383616 reaction equation
N[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:3]=1[I:25].C(ON=O)(C)(C)C>O1CCCC1>[Cl:13][C:12]1[CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=[C:8]([Cl:18])[C:7]=1[N:6]1[CH:2]=[C:3]([I:25])[C:4]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[N:5]1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 21188116HCID 21188116, compound

Product 1

HCID 21188064HCID 21188064, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)4iodo-3-phenylpyrazole (2.5 g) in tetrahydrofuiran (50 ml) at 65° C. was added dropwise t-butylnitrite (3 g) in tetrahydrofuran (20 ml) over a period of 30 minutes and heating continued for 3 hours then left at room temperature overnight. The reaction mixture was evaporated to an oil which was purified by column chromatography on silica gel eluted with dichloromethane. Combination and evaporation of appropriate fractions, followed by further column chromatography on silica gel eluted with hexane, then hexane containing 5% ethyl acetate and finally hexane containing 10% ethyl acetate. Combination and evaporation of appropriate fractions gave the title compound as a cream solid m.p. 88-89° C.

Workup

  1. temperatureheating
  2. waitthen left at room temperature overnight
  3. customThe reaction mixture was evaporated to an oil which
  4. customwas purified by column chromatography on silica gel
  5. washeluted with dichloromethane
  6. customCombination and evaporation of appropriate fractions
  7. washeluted with hexane
  8. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-1a418f3d11034481bc1df4b557480749
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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