m-Hydroxybenzohydrazide → 3-[5-(4-Chloro-3-trifluoromethyl-phenylamino)-4h[1,2,4]triazol-3-yl]-phenol

HRID 387453

반응식

HRID 387453 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][NH2:8])=O.I.CS[C:15](=[NH:28])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:18]=1>N1C=CC=CC=1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:15]2[NH:28][C:5]([C:4]3[CH:3]=[C:2]([OH:1])[CH:11]=[CH:10][CH:9]=3)=[N:7][N:8]=2)=[CH:18][C:19]=1[C:24]([F:25])([F:26])[F:27]

참가 물질

4

반응물 2

HCID 79889m-HydroxybenzohydrazideHCID 1785040011-[4-chloro-3-(trifluoromethyl)phenyl]-S-methylisothiourea hydroiodide

생성물 1

HCID 1785159893-[5-(4-Chloro-3-trifluoromethyl-phenylamino)-4h[1,2,4]triazol-3-yl]-phenol수율 31.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

3-hydroxybenzoic acid hydrazide (2.98 g, 19.58 mmol) and S-methyl N-[4-chloro-3-(trifluoromethyl)phenyl]isothiourea hydroiodide (7.78 g, 19.63 mmol) were suspended in 40 mL of anhydrous pyridine. The reaction mixture was refluxed for 18 hours, during which time it changed color from yellow into dark-red. Then it was cooled down to ambient temperature and poured with stirring into 250 mL of ice-water. The aqueous solution was decanted and the oily residue was purified by silica gel chromatography on Isco column using 0=>50% gradient of ethyl acetate in hexane. Solvent was removed in vacuo to give the title product as a white solid (2.176 g). 31.3% yield.

후처리

  1. temperatureThe reaction mixture was refluxed for 18 hours, during which time it
  2. additionpoured
  3. customThe aqueous solution was decanted
  4. customthe oily residue was purified by silica gel chromatography on Isco column
  5. customSolvent was removed in vacuo

출처 및 근거

ORD 기록
ord-854ec41e5fb84ca4ae891ea9a3bcaa1f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372971B2

연결된 노트

불러오는 중…