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

HRID 1528337노트

반응식

HRID 1528337 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-80dfea344039410cbb2dbd8935c859b4
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090600B2

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