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

HRID 452573ノート

反応式

HRID 452573 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-9a719dbbe32c4adcb817e72b8d34ec10
出典データセット
uspto-grants-2013_07
特許番号
US08492388B2

反応ノート

読み込み中…