Methyl iodide → 5-Methyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513596ノート

反応式

HRID 513596 の反応式
[CH:1]1[C:18]2[C:5](=[C:6]3[C:15](=[CH:16][CH:17]=2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[S:8](=[O:20])(=[O:19])[NH:7]3)[N:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:23]I>C1COCC1>[CH3:23][N:7]1[S:8](=[O:19])(=[O:20])[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15]2[C:6]1=[C:5]1[C:18](=[CH:17][CH:16]=2)[CH:1]=[CH:2][CH:3]=[N:4]1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6591015H-quinolino[8,7-c][1,2]benzothiazine 6,6-dioxide2 回

生成物 1

HCID 681832885-Methyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide収率 52%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5H-6-Thia-4,5-diaza-chrysene 6,6-dioxide (Example Compound 2) (50 mg, 0.18 mmol) was added to solution of NaH (60% dispersion in mineral oil; 11 mg, 0.27 mmol) dissolved in dry THF (3 ml), under argon, at 0° C., and the mixture was stirred for 15 min. Methyliodide (29 mg, 0.22 mmol) was added and the reaction was allowed to warm to room temperature and stirring continued for 12 h. After completion of the reaction (monitored by TLC), the solvent was removed in vacuo. The residue was dissolved in EtOAc, washed with water and brine. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with n-hexane/EtOAc (3:1) as the eluent to give the title compound (27 mg, 52%).

後処理

  1. stirringstirring
  2. waitcontinued for 12 h
  3. customAfter completion of the reaction (monitored by TLC)
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with water and brine
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by column chromatography with n-hexane/EtOAc (3:1) as the eluent

出典と根拠

ORDレコード
ord-7b4380312f4b48d1ab27e331031c4a83
出典データセット
uspto-grants-2015_08
特許番号
US09102688B2

反応ノート

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