Isoamyl Nitrite → HCID 66650354、化合物

HRID 558479ノート

反応式

HRID 558479 の反応式
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]

参加物

5

反応物 2

HCID 8053Isoamyl NitriteHCID 66650419Amino-5-ethoxy-4-trifluoromethyl-benzonitrile

生成物 1

HCID 66650354HCID 66650354、化合物収率 85%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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].

後処理

  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)

出典と根拠

ORDレコード
ord-0347bb161366413bb635beba5177802d
出典データセット
uspto-grants-2011_11
特許番号
US08063048B2

反応ノート

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