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Triethylamine → HCID 57749238, 화합물

HRID 1874336
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HRID 1874336 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11](C(O)=O)=[N:12][CH:13]=1)([O-:3])=[O:2].C1(P([N:34]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>C(O)(C)(C)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:34])=[N:12][CH:13]=1)([O-:3])=[O:2]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 577493765-(3-Nitrophenoxy)pyridine-2-carboxylic acid

생성물 1

HCID 57749238HCID 57749238, 화합물수율 63%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

A mixture of 5-(3-nitrophenoxy)pyridine-2-carboxylic acid (10.4 g, 40.0 mmol), diphenylphosphoryl azide (10.8 mL, 50.0 mmol), triethylamine (6.92 mL, 50.0 mmol) and tert-butanol (200 mL) was stirred at room temperature for 3 hr, and then stirred with heating under reflux for 15 hr. The reaction mixture was concentrated under reduced pressure, trifluoroacetic acid (20 mL) was added to the residue, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, 8N aqueous sodium hydroxide solution (70 mL) was added to the residue, and the mixture was stirred with heating under refluxing conditions for 3 hr. After extraction with ethyl acetate (×3), the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was dried to give the title compound (5.80 g, 63%) as a white solid.

후처리

  1. stirringstirred
  2. temperaturewith heating
  3. temperatureunder reflux for 15 hr
  4. concentrationThe reaction mixture was concentrated under reduced pressure, trifluoroacetic acid (20 mL)
  5. additionwas added to the residue
  6. stirringthe mixture was stirred at room temperature for 1 hr
  7. concentrationThe reaction mixture was concentrated under reduced pressure, 8N aqueous sodium hydroxide solution (70 mL)
  8. additionwas added to the residue
  9. stirringthe mixture was stirred
  10. temperaturewith heating under refluxing conditions for 3 hr
  11. extractionAfter extraction with ethyl acetate (×3)
  12. washthe organic layer was washed with saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationfiltrated
  15. concentrationThe filtrate was concentrated under reduced pressure
  16. customthe residue was dried

출처 및 근거

ORD 기록
ord-1edc16a51c604bff97402b02e5d9217a
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08304557B2

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