Ammonium Chloride → Tert-butyl 5-aminothiophene-2-carboxylate

HRID 59747노트

반응식

HRID 59747 반응식
[N+:1]([C:4]1[S:8][C:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:1][C:4]1[S:8][C:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:6][CH:5]=1

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 23344844Tert-butyl 5-nitrothiophene-2-carboxylate

생성물 1

HCID 86703850Tert-butyl 5-aminothiophene-2-carboxylate수율 76.4%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

To a suspension of tert-butyl 5-nitrothiophene-2-carboxylate (Int. 54) (2.230 g, 9.73 mmol) in a mixture of EtOH (60 ml) and water (30 ml), iron powder (3.26 g, 58.4 mmol) and ammonium chloride (0.364 g, 6.81 mmol) were added. The reaction was stirred at 80° C. for 3 hours and then at RT overnight. The mixture was filtered through a celite pad and the filtrate was evaporated to dryness. The crude was then dissolved in EtOAc and washed with brine; the organic phase was dried over sodium sulfate and the solvent evaporated under vacuum. The residue was purified by filtration through a silica gel cartridge (petroleum ether/EtOAc=9/1 to 6/4) to yield tert-butyl 5-aminothiophene-2-carboxylate (Int. 55) (1.481 g, 7.43 mmol, MS/ESI+200.0 [MH]+).

후처리

  1. additionwere added
  2. customat RT
  3. customovernight
  4. filtrationThe mixture was filtered through a celite pad
  5. customthe filtrate was evaporated to dryness
  6. dissolutionThe crude was then dissolved in EtOAc
  7. washwashed with brine
  8. dry with materialthe organic phase was dried over sodium sulfate
  9. customthe solvent evaporated under vacuum
  10. filtrationThe residue was purified by filtration through a silica gel cartridge (petroleum ether/EtOAc=9/1 to 6/4)

출처 및 근거

ORD 기록
ord-0449aa2472d54828938340e2b80d282d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440954B2

반응 노트

불러오는 중…