Tert-Butyl nitrite → HCID 70239777, compound

HRID 1383580Notes

Reaction equation

HRID 1383580 reaction equation
Br[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]#[C:22][Si:23]([CH3:26])([CH3:25])[CH3:24].N(OC(C)(C)C)=O>O1CCCC1>[C:19]([C:4]1[C:3]([CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[CH:2][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])[N:5]=1)#[N:20]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 21188048HCID 21188048, compound

Product 1

HCID 70239777HCID 70239777, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-aniino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trimethylsilylethynylpyrazole (30 mg, the compound of Example C1) in tetrahydrofuran (10 ml) was added dropwise over five minutes t-butyl nitrite (0.025 ml). The nixture was heated under reflux for 30 minutes, then cooled and evaporated. The residue was purified by column chromatography on silica gel (50 g) eluted with dichloromethane: hexane (1:4) to provide the title compound as a white solid m.p. 128-9° C.

Workup

  1. temperatureThe nixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturecooled
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (50 g)
  6. washeluted with dichloromethane: hexane (1:4)

Sources & evidence

ORD record
ord-2402e0949d2e4daba908a5c8a3a82ec9
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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