tert-Butanol → 5-Amino-2-(2-methylpropyl)benzonitrile

HRID 1744519

반응식

HRID 1744519 반응식
C(O)(C)(C)C.[C:6]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[CH2:17][CH:18]([CH3:20])[CH3:19])C(O)=O)#[N:7].C1(P([N:35]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C(N(CC)CC)C>[NH2:35][C:10]1[CH:14]=[CH:15][C:16]([CH2:17][CH:18]([CH3:20])[CH3:19])=[C:8]([CH:9]=1)[C:6]#[N:7]

참가 물질

5

반응물 3

HCID 6386tert-ButanolHCID 199401P,P-Diphenylphosphinic azideHCID 222281753-Cyano-4-isobutylbenzoic acid

생성물 1

HCID 222279325-Amino-2-(2-methylpropyl)benzonitrile수율 82.3%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

To tert-butyl alcohol containing 3-cyano-4-isobutylbenzoic acid (8.5 g) and triethylamine (4.2 g) was added diphenylphosphoryl azide (11.5 g) at room temperature and the mixture was stirred at a refluxing temperature for 1 h. The solvent was evaporated under reduced pressure. To the residue was added aqueous potassium carbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. To the residue were added 6N hydrochloric acid (10 ml) and methanol (100 ml) and the mixture was stirred at a refluxing temperature for 1 h. The solvent was evaporated under reduced pressure. To the residue was added aqueous sodium hydroxide solution and the mixture was extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. n-Hexane was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of diisopropyl ether-n-hexane to give the title compound (6.0 g), melting point: 68° C.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. additionTo the residue was added aqueous potassium carbonate solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customafter which the solvent was evaporated under reduced pressure
  7. additionTo the residue were added 6N hydrochloric acid (10 ml) and methanol (100 ml)
  8. stirringthe mixture was stirred at a refluxing temperature for 1 h
  9. customThe solvent was evaporated under reduced pressure
  10. additionTo the residue was added aqueous sodium hydroxide solution
  11. extractionthe mixture was extracted with toluene
  12. washThe organic layer was washed with saturated brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. customafter which the solvent was evaporated under reduced pressure
  15. additionn-Hexane was added to the residue
  16. customcrystallization
  17. customThe crystals were recrystallized from a mixed solvent of diisopropyl ether-n-hexane

출처 및 근거

ORD 기록
ord-c844ba267921441aaf6c294725757710
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015218B1

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