Tert-Butyl nitrite → HCID 14280195, compound

HRID 975522Notes

Reaction equation

HRID 975522 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]([F:22])([F:21])[F:20])[C:3]=1[C:23]#[N:24].N(OC(C)(C)C)=O>O1CCCC1>[C:23]([C:3]1[C:4]([C:19]([F:22])([F:20])[F:21])=[N:5][N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:16])([F:17])[F:15])=[CH:11][C:12]=2[Cl:13])[CH:2]=1)#[N:24]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitrite2×HCID 101349005-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 14280195HCID 14280195, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-amino-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole (2.33 g) in dry tetrahydrofuran (30 ml) was added with stirring at room temperature, a solution of tert-butyl nitrite (1.36 ml) in dry tetrahydrofuran (5 ml) during 2 minutes. The solution was then heated under reflux for 1 hour and cooled, and additional tert-butyl nitrite (2.72 ml) was added. The solution was heated under reflux for 30 minutes, and left to cool overnight. Evaporation in vacuo gave an orange oil, which was purified by chromatography on silica (Merck, 40-230 mesh, 0.7 kg cm-2) eluting with dichloromethane-hexane (1:1). The product was finally recrystallized from hexane to give 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole, m.p. 121°-123° C., as white crystals.

Workup

  1. temperatureThe solution was then heated
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. temperatureThe solution was heated
  5. temperatureunder reflux for 30 minutes
  6. waitleft
  7. temperatureto cool overnight
  8. customEvaporation in vacuo
  9. customgave an orange oil, which
  10. customwas purified by chromatography on silica (Merck, 40-230 mesh, 0.7 kg cm-2)
  11. washeluting with dichloromethane-hexane (1:1)
  12. customThe product was finally recrystallized from hexane

Sources & evidence

ORD record
ord-1d880e4c97ad4598b4d830a12171c83a
Source dataset
uspto-grants-1997_03
Patent number
US05608077

Reaction notes

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