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

HRID 1664177ノート

反応式

HRID 1664177 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1840b3cc038d4aaa9dc47b6ca99e6837
出典データセット
uspto-grants-2011_10
特許番号
US08039458B2

反応ノート

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