Potassium Iodide → but-3-ynyl N-[6-[[(Z)-[cyano(phenyl)methylidene]amino]oxymethyl]-2-pyridinyl]carbamate

HRID 1430576ノート

反応式

HRID 1430576 の反応式
[CH2:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]Cl)[N:9]=1)[CH2:2][C:3]#[CH:4].[I-].[K+].[C:19](/[C:21](=[N:28]\[O-:29])/[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)#[N:20].[Na+]>C(#N)C.CN(C=O)C>[CH2:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:29]/[N:28]=[C:21](\[C:19]#[N:20])/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:9]=1)[CH2:2][C:3]#[CH:4]

参加物

6

反応物 3

HCID 4875Potassium IodideHCID 23690115sodium (Z)-N-oxidobenzenecarboximidoyl cyanideHCID 57407594But-3-in-1-yl[6-(chloromethyl)pyridin-2-yl]carbamate

生成物 1

HCID 57408013but-3-ynyl N-[6-[[(Z)-[cyano(phenyl)methylidene]amino]oxymethyl]-2-pyridinyl]carbamate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

Phenylacetonitrile (9.72 g, 82.97 mmol) was metered into a suspension of 3.31 g (82.97 mmol) of NaOH in 60 ml of ethanol. Following the complete addition, 11.66 g (99.56 mmol) of isopentyl nitrite were metered in dropwise at temperatures of 15° C. The mixture was then stirred for a further 2 hours at this temperature. The reaction mixture was diluted with 300 ml of diethyl ether, and the precipitated solid was filtered off and washed twice with in each case 50 ml of diethyl ether. The white salt sodium {[(Z)-cyano(phenyl)methylene]amino}oxidanide (7.89 g, 56% yield) can be dried in vacuo or be further used directly. 1.49 g (6.24 mmol) of but-3-yn-1-yl[6-(chloromethyl)pyridin-2-yl]carbamate and 103 mg (0.624 mmol) of potassium iodide were added to a solution of 1.05 g (6.24 mmol) of sodium {[(Z)-cyano(phenyl)methylene]amino}oxidanide in 25 ml of acetonitrile and 10 ml of DMF. The reaction mixture was stirred for 7 h at room temperature, the solvent was removed in vacuo and the residue was dissolved in 100 ml of ethyl acetate. The organic phase was washed with water and dried over MgSO4. After removing the solvent, 2.21 g (99% yield, only 1 oxime isomer) of but-3-yn-1-yl{6-[({[(Z)-cyano(phenyl)methylene]-amino}oxy)methyl]pyridin-2-yl}carbamate were isolated as a colourless solid.

後処理

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 100 ml of ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. customAfter removing the solvent, 2.21 g (99% yield, only 1 oxime isomer) of but-3-yn-1-yl{6-[({[(Z)-cyano(phenyl)methylene]-amino}oxy)methyl]pyridin-2-yl}carbamate
  6. customwere isolated as a colourless solid

出典と根拠

ORDレコード
ord-4d9dc442b84946e2958a05ab8890f0a9
出典データセット
uspto-grants-2015_01
特許番号
US08940899B2

反応ノート

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