Isoamyl Nitrite → HCID 86086327, compound

HRID 1293596Notes

Reaction equation

HRID 1293596 reaction equation
N[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[C:7]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:6][C:3]=1[C:4]#[N:5].N(OCCC(C)C)=O>C1COCC1.CC(OC)(C)C>[F:17][C:16]([F:18])([F:19])[CH2:15][O:14][C:7]1[CH:6]=[C:3]([CH:2]=[CH:9][C:8]=1[C:10]([F:13])([F:11])[F:12])[C:4]#[N:5]

Participants

5

Reactant 2

HCID 8053Isoamyl NitriteHCID 86086326HCID 86086326, compound

Product 1

HCID 86086327HCID 86086327, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 2-amino-5-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzonitrile from step 4 (14.47 g, 50.9 mmol) in dry THF (153 mL) was added isoamyl nitrite (15.0 mL, 112.0 mmol), and the mixture was refluxed for 20 h. The solvent was removed in vacuum to give an orange oil, which was dissolved in TBME, washed with 1 N HCl, sat. NaHCO3-sol. and brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown solid (15.05 g), which was purified by Kugelrohr distillation (up to 155° C. bath temperature at 1.2 mbar) to give the title compound as alight yellow solid (10.83 g, 79%). MS (EI) 269 [M].

Workup

  1. temperaturethe mixture was refluxed for 20 h
  2. customThe solvent was removed in vacuum
  3. customto give an orange oil, which
  4. washwashed with 1 N HCl, sat. NaHCO3-sol
  5. dry with materialand brine, dried over Na2SO4
  6. customRemoval of the solvent in vacuum
  7. waitleft a brown solid (15.05 g), which
  8. distillationwas purified by Kugelrohr distillation (up to 155° C. bath temperature at 1.2 mbar)

Sources & evidence

ORD record
ord-f861f1335c2a474fbf81aa986af0d63e
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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