Hydroxyamine hydrochloride → N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-[3-(trifluoromethoxy)phenyl]methanimine

HRID 452573

반응식

HRID 452573 반응식
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=2)=O)=[N:5][N:4]=[N:3]1.Cl.[NH2:21][OH:22]>N1C=CC=CC=1.C(OCC)(=O)C>[OH:22][N:21]=[C:7]([C:6]1[N:2]([CH3:1])[N:3]=[N:4][N:5]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=1

참가 물질

5

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 67075092(1-methyl-1H-tetrazol-5-yl)[3-(trifluoromethoxy)phenyl]methanone

생성물 1

HCID 136337385N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-[3-(trifluoromethoxy)phenyl]methanimine수율 92%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

To a stirred solution of (1-methyl-1H-tetrazol-5-yl)[3-(trifluoromethoxy)phenyl]methanone (5.12 g, 16.2 mmol) in dry pyridine (25 mL) was added hydroxylamine hydrochloride (2.81 g, 40.4 mmol). The mixture was stirred at 70° C. for 3 h, then left to stand overnight. After concentration of the reaction mixture in vacuo, the residue was diluted with ethyl acetate (100 mL) and washed with water (50 mL). The aqueous layer was extracted with ethyl acetate (50 mL), the combined organic layers dried (MgSO4), concentrated in vacuo and dissolved in toluene. A crystalline precipitate appeared, which was filtered off to afford N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-[3-(trifluoromethoxy)phenyl]methanimine as a white solid [4.33 g, yield 92%; HPLC/MS:m/z=288 (M+H); log P(HCOOH)=2.37].

후처리

  1. waitleft
  2. waitto stand overnight
  3. washwashed with water (50 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (50 mL)
  5. dry with materialthe combined organic layers dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. dissolutiondissolved in toluene
  8. filtrationwhich was filtered off

출처 및 근거

ORD 기록
ord-9a719dbbe32c4adcb817e72b8d34ec10
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492388B2

연결된 노트

불러오는 중…