Potassium Iodide → 6-(tert-Butyl)-3-methylselenopheno[3,2-d]1,2,3-triazin-4-one

HRID 1097225ノート

反応式

HRID 1097225 の反応式
[C:1]([C:5]1[Se:13][C:12]2[C:11](=[O:14])[NH:10][N:9]=[N:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:15](=O)([O-])[O-].[K+].[K+].IC.[I-].[K+]>CC(C)=O>[C:1]([C:5]1[Se:13][C:12]2[C:11](=[O:14])[N:10]([CH3:15])[N:9]=[N:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136331513HCID 136331513、化合物

生成物 1

HCID 595472216-(tert-Butyl)-3-methylselenopheno[3,2-d]1,2,3-triazin-4-one収率 47.6%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 6-(tert-butyl)-3H-selenopheno[3,2-d]1,2,3-triazin-4-one (2.0 g, 7.78 mmol) in acetone (70 mL) was added sequentially potassium carbonate (2.14 g, 15.56 mmol), iodomethane (0.58 mL, 9.3 mmol) and potassium iodide (catalytic) at rt and the mixture was stirred at rt for 16 h. The solution was filtered and the solids were washed with acetone. Acetone was evaporated under reduced pressure and the residue was chromatographed over silica gel column using chloroform-methanol (95:05) as eluents to give the product as a off-white color solid (1.0 g, 47%), which was recrystallized from chloroform-methanol (700 mg, 34%), mp 98-100° C. IR (neat) νmax 2961, 1679, 1242, 1220, 1001, 969 cm−1; 1H NMR (400 MHz, CDCl3): δ 7.58 (1H, s, H-7), 4.04 (3H, s, —NCH3), 1.48 (9H, s, tert-butyl); 13C NMR (100 MHz, CDCl3): δ 176.0, 157.5, 154.7, 128.8, 121.5, 37.5, 37.3, 32.5; LC-MS (positive ion mode): m/z 292, 294 (M+Na)+.

後処理

  1. filtrationThe solution was filtered
  2. washthe solids were washed with acetone
  3. customAcetone was evaporated under reduced pressure
  4. customthe residue was chromatographed over silica gel column

出典と根拠

ORDレコード
ord-832ea98921b94f1c9bb17697149e37de
出典データセット
uspto-grants-2012_03
特許番号
US08143237B2

反応ノート

読み込み中…