Methyl iodide → 6-Amino-4-furan-2-yl-2-methylsulfanyl-nicotinonitrile

HRID 1356048ノート

反応式

HRID 1356048 の反応式
[NH2:1][C:2]1[NH:7][C:6](=[S:8])[C:5]([C:9]#[N:10])=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[CH:3]=1.[CH3:16][O-].[Na+].CI>CO>[NH2:1][C:2]1[CH:3]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[C:5]([C:9]#[N:10])=[C:6]([S:8][CH3:16])[N:7]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 185073536-Amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile

生成物 1

HCID 185075176-Amino-4-furan-2-yl-2-methylsulfanyl-nicotinonitrile収率 71%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of 150 mg (0.69 mmol) 6-amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile in 3 ml methanol were added 0.13 ml (0.69 mmol) sodium methylate solution (5.4M in ethanol) and 0.04 ml (0.69 mmol) methyl iodide and the reaction mixture stirred at room temperature for 30 minutes. The reaction mixture was then concentrated in vacuo and the residue partitioned between dichloromethane and water. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was triturated in ether to afford 113 mg (71%) 6-amino-4-furan-2-yl-2-methylsulfanyl-nicotinonitrile as a brown crystalline solid. ES-MS m/e (%): 232 (M+H+, 100).

後処理

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue partitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated in ether

出典と根拠

ORDレコード
ord-1b3792b8994d4589aad7a26e533721d2
出典データセット
uspto-grants-2003_07
特許番号
US06586441B2

反応ノート

読み込み中…