Tert-Butyl nitrite → HCID 9887618, compound

HRID 1108839Notes

Reaction equation

HRID 1108839 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]#[N:20])[C:3]=1[C:21]1[CH:25]=[CH:24][O:23][C:22]=1[Cl:26].N(OC(C)(C)C)=O>O1CCCC1>[Cl:26][C:22]1[O:23][CH:24]=[CH:25][C:21]=1[C:3]1[C:4]([C:19]#[N:20])=[N:5][N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:15])[F:16])=[CH:9][C:8]=2[Cl:18])[CH:2]=1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 221209155-Amino-4-(2-chlorofuran-3-yl)-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

Product 1

HCID 9887618HCID 9887618, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-amino-4-(2-chlorofuran-3-yl)-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (0.204 g) in tetrahydrofuran (3 ml) was added t-butyl nitrite (171.8 μl). The mixture was heated to 65° C. for 1 hour, then cooled and evaporated. The residue was purified by column chromatography on silica gel (10 g) eluted with hexane containing increasing amounts of dichloromethane (up to 100%). Combination and evaporation of appropriate fraction gave the title compound as a white solid, m.p. 125° C.

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue was purified by column chromatography on silica gel (10 g)
  4. washeluted with hexane containing
  5. temperatureincreasing amounts of dichloromethane (up to 100%)
  6. customCombination and evaporation of appropriate fraction

Sources & evidence

ORD record
ord-6c1ca3cd8fd04244ad5965c943fe9eb2
Source dataset
uspto-grants-2000_05
Patent number
US06069157

Reaction notes

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