Hydroxyamine hydrochloride → 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime

HRID 475095노트

반응식

HRID 475095 반응식
[CH3:1][O:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[CH:18]=O.CC([O-])=O.[Na+].Cl.[OH:26][NH2:27]>CO>[CH3:1][O:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[CH:18]=[N:27][OH:26]

참가 물질

5

반응물 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866946904-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde

생성물 1

HCID 866946914-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime수율 93%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A 1 L three-necked round bottom flask equipped with a magnetic stirrer was dried and cooled under a stream of nitrogen then charged with 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde (15 g, 0.057 mol, 1.0 equiv.), NaOAc (15.67 g, 0.12 mol, 2.0 equiv.), hydroxyamine hydrochloride (8.01 g, 0.12 mol, 2.0 equiv.) and MeOH (300 mL) and the reaction mixture was stirred at RT for 1 h. The reaction mixture was then concentrated and the residue was dissolved in EtOAc (1000 mL). The organic layer was washed with water (2×300 mL) and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime (14.5 g, 93% yield).

후처리

  1. customA 1 L three-necked round bottom flask equipped with a magnetic stirrer
  2. customwas dried
  3. temperaturecooled under a stream of nitrogen
  4. concentrationThe reaction mixture was then concentrated
  5. dissolutionthe residue was dissolved in EtOAc (1000 mL)
  6. washThe organic layer was washed with water (2×300 mL) and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8313ca22fd354b5fbaa014643850c97b
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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