Triethylamine → 1-(2-Bromo-5-fluorophenyl)-1H-1,2,4-triazol-5(4H)-one

HRID 1664177노트

반응식

HRID 1664177 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][N:10]=[CH:11]C(O)=O.C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[OH-].[K+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N:9]1[C:20](=[O:29])[NH:17][CH:11]=[N:10]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 199401P,P-Diphenylphosphinic azideHCID 674393932-(2-(2-Bromo-5-fluorophenyl)hydrazono)acetic acid

생성물 1

HCID 1360941091-(2-Bromo-5-fluorophenyl)-1H-1,2,4-triazol-5(4H)-one수율 67%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a stirred suspension of 2-(2-(2-bromo-5-fluorophenyl)hydrazono)acetic acid (2.65 g, 10.2 mmol) in toluene (80 mL) was added triethylamine (1.42 mL, 10.2 mmol) and diphenylphosphoryl azide (2.2 mL, 10.2 mmol). The resulting mixture was slowly heated to reflux temperature and the reflux was maintained for 1 h. The clear orange solution was cooled and then poured onto 10% aqueous KOH (100 mL). The basic extract was acidified (pH 1) with concentrated HCl. The precipitate that formed was collected by filtration, washed with water and dried at reduced pressure to afford the title compound as a yellow solid (1.75 g, 67% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 11.87 (1H, s), 8.10-8.08 (1H, m), 7.83 (1H, dd, J=8.8, 5.8 Hz), 7.50 (1 H, dd, J=9.1, 3.0 Hz), 7.34 (1H, td, J=8.6, 3.0 Hz); LCMS (+ESI, M+H+) m/z 258-260.

후처리

  1. temperatureThe resulting mixture was slowly heated
  2. temperatureto reflux temperature
  3. temperaturethe reflux was maintained for 1 h
  4. temperatureThe clear orange solution was cooled
  5. extractionThe basic extract
  6. customThe precipitate that formed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customdried at reduced pressure

출처 및 근거

ORD 기록
ord-1840b3cc038d4aaa9dc47b6ca99e6837
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039458B2

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