Potassium Iodide → tert-butyl N-[6-[[(Z)-[cyano(phenyl)methylidene]amino]oxymethyl]-2-pyridinyl]carbamate

HRID 1528337ノート

反応式

HRID 1528337 の反応式
[OH:1]/[N:2]=[C:3](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)\[C:4]#[N:5].Cl[CH2:13][C:14]1[N:19]=[C:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=[CH:16][CH:15]=1.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.CN(C=O)C>[C:4](/[C:3](=[N:2]\[O:1][CH2:13][C:14]1[N:19]=[C:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH:17]=[CH:16][CH:15]=1)/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)#[N:5]

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 5464219N-Hydroxybenzimidoyl cyanideHCID 21851761tert-Butyl (6-(chloromethyl)pyridin-2-yl)carbamate

生成物 1

HCID 140660333tert-butyl N-[6-[[(Z)-[cyano(phenyl)methylidene]amino]oxymethyl]-2-pyridinyl]carbamate収率 80%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of (2Z)-(hydroxyimino)(phenyl)acetonitrile (2.5 g, 17.10 mmol, 1 eq.) in 100 ml of acetonitrile and 10 ml DMF was added tert-butyl [6-(chloromethyl)pyridin-2-yl]carbamate (4.15 g, 17.10 mmol, 1 eq.) followed by potassium iodide (283 mg, 1.71 mmol, 0.1 eq.) and caesium carbonate (8.36 g, 25.65 mmol, 1.5 eq.). The reaction was stirred overnight at room temperature. The solvent was than evaporated and the residue dissolved in EtOAc (100 ml). The organic layer was washed with H2O and dried over MgSO4 then concentrated. tert-butyl {6-[({[(Z)-cyano(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (5.39 g, 80% yield, only 1 oxime isomer) was obtained as a white solid.

後処理

  1. customthan evaporated
  2. dissolutionthe residue dissolved in EtOAc (100 ml)
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationthen concentrated

出典と根拠

ORDレコード
ord-80dfea344039410cbb2dbd8935c859b4
出典データセット
uspto-grants-2015_07
特許番号
US09090600B2

反応ノート

読み込み中…