Tert-Butyl nitrite → HCID 21188047, compound

HRID 1383609Notes

Reaction equation

HRID 1383609 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]([CH3:19])[C:3]=1[I:20].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:20])[C:4]([CH3:19])=[N:5]1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 22618399HCID 22618399, compound

Product 1

HCID 21188047HCID 21188047, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-amino -1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodo-3-methylpyrazole (2.85 g) in tetrahydrofuran (35 ml) at 0° C. was added dropwise t-butylnitrite (2.33 ml). The reaction mixture was allowed to warm to room temperature and then heated under reflux for 1.5 hours. The reaction mixture was evaporated and the residue purified by column chromatography on silica gel eluted with dichloromethane: hexane (1:1). Combination and evaporation of suitable fractions provided a yellow oil which was further purified by column chromatography on silica gel eluted with dichloromethane: hexane (1:2). Combination and evaporation of suitable fractions provided the title compound as a white solid, m.p. 118.5-119.4° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. customThe reaction mixture was evaporated
  4. customthe residue purified by column chromatography on silica gel
  5. washeluted with dichloromethane: hexane (1:1)
  6. customCombination and evaporation of suitable fractions
  7. customprovided a yellow oil which
  8. customwas further purified by column chromatography on silica gel
  9. washeluted with dichloromethane: hexane (1:2)
  10. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-35481554bfab4dd084d5c5387154cba8
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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