Isoamyl Nitrite → HCID 66650354, compound

HRID 268917Notes

Reaction equation

HRID 268917 reaction equation
N[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[C:7]([O:14][CH2:15][CH3:16])=[CH:6][C:3]=1[C:4]#[N:5].N(OCCC(C)C)=O>C1COCC1.C([O-])(O)=O.[Na+]>[CH2:15]([O:14][C:7]1[CH:6]=[C:3]([CH:2]=[CH:9][C:8]=1[C:10]([F:11])([F:12])[F:13])[C:4]#[N:5])[CH3:16]

Participants

5

Reactant 2

HCID 8053Isoamyl NitriteHCID 66650419HCID 66650419, compound

Product 1

HCID 66650354HCID 66650354, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-amino-5-ethoxy-4-trifluoromethyl-benzonitrile from step 4 (31.62 g, 137.4 mmol) in dry THF (410 mL) was added isoamyl nitrite (40.4 mL, 302 mmol), and the mixture was refluxed for 16 h. The solvent was removed in vacuum to give an orange oil, which was dissolved in sat. NaHCO3-sol., extracted three times with diethyl ether. The combined organic layers were washed with 1 N HCl and brine, dried over Na2SO4. Removal of the solvent in vacuum left an orange oil, which was purified by double Kugelrohr distillation (up to 160° C. bath temperature at 1.5 mbar) to give the title compound as a light yellow solid (25.06 g, 85%). MS (EI) 185.1 [M].

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. customThe solvent was removed in vacuum
  3. customto give an orange oil, which
  4. extraction, extracted three times with diethyl ether
  5. washThe combined organic layers were washed with 1 N HCl and brine
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent in vacuum
  8. waitleft an orange oil, which
  9. distillationwas purified by double Kugelrohr distillation (up to 160° C. bath temperature at 1.5 mbar)

Sources & evidence

ORD record
ord-3ab9b616bb824cb6b8494e4f2d7f1c51
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

Loading…