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Pyridine → 2-(2H-Benzo[D][1,2,3]triazol-2-YL)ethanamine

HRID 233734
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HRID 233734 반응식
[N:1]1[N:2]([CH2:10][CH2:11]O)[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[N:13]1C=CC=CC=1.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O>C(OCC)C>[N:1]1[N:2]([CH2:10][CH2:11][NH2:13])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 817804HCID 817804, 화합물

생성물 1

HCID 104872022-(2H-Benzo[D][1,2,3]triazol-2-YL)ethanamine수율 44,791.699%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-50 °C

실험 절차

4.70 g Of the 2-(2-benzotriazolyl)ethanol (28.8 mmol) was dissolved in 200 ml diethyl ether and 2.28 g pyridine (28.8 mmol) was added. The mixture was cooled to -50° C., and 8.18 g triflic anhydride (29 mmol) was added. The mixture was removed from the cooling bath, and was allowed to reach room temperature. The mixture was filtered under dry conditions and added to a cold -40° C. solution of ca 150 ml ammonia in 50 ml diethyl ether. This mixture was allowed to reach room temperature, and ether was removed. 50 ml 2M HCl was added, and this mixture was washed with methylene chloride. The aqueous phase was made basic by addition of 50 ml 25% sodium hydroxide and extracted with 3×25 ml methylene chloride. Evaporation of the solvent gave 2.10 g 2-(2-benzotriazolyl)ethylamine (12.9 mol). This amine was used in the next step without further purification.

후처리

  1. customThe mixture was removed from the cooling bath
  2. customto reach room temperature
  3. filtrationThe mixture was filtered under dry conditions
  4. additionadded to a cold -40° C. solution of ca 150 ml ammonia in 50 ml diethyl ether
  5. customto reach room temperature
  6. customether was removed
  7. addition50 ml 2M HCl was added
  8. washthis mixture was washed with methylene chloride
  9. additionThe aqueous phase was made basic by addition of 50 ml 25% sodium hydroxide
  10. extractionextracted with 3×25 ml methylene chloride
  11. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-949a319935e546c5963c3f34f22892aa
출처 데이터셋
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05593993

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