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

HRID 1097225Notes

Reaction equation

HRID 1097225 reaction equation
[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]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136331513HCID 136331513, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-832ea98921b94f1c9bb17697149e37de
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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