Methyl iodide → HCID 59547208, compound

HRID 1097235Notes

Reaction equation

HRID 1097235 reaction equation
[N:1]1[C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[Se:9][C:5]=2[C:4](=[O:14])[NH:3][N:2]=1.[C:15](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH3:15][N:3]1[C:4](=[O:14])[C:5]2[Se:9][C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[C:6]=2[N:1]=[N:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136155074HCID 136155074, compound

Product 1

HCID 59547208HCID 59547208, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3H-benzo[b]1,2,3-triazino[4,5-d]selenophen-4-one (200 mg, 0.8 mmol) in acetone (50 mL) was added sequentially potassium carbonate (400 mg, 1.6 mmol), iodomethane (0.1 mL, 0.9 mmol) and a catalytic amount of PEG-400 was added 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 hexane-chloroform (70:30) as eluents to give the product as a off-white solid (120 mg, 47%), mp 190-192° C. IR (neat) νmax 3431, 1673, 1220, 1021 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.56-8.58 (1H, m, H-9), 7.98-8.01 (1H, m, H-6), 7.58-7.66 (2H, m, H-7,8), 4.13 (3H, s, —NCH3); 13C NMR (100 MHz, CDCl3): δ 155.5, 152.8, 142.3, 135.3, 130.4, 129.8, 126.4, 126.2, 126.0, 37.8; LC-MS (positive ion mode): m/z 286, 288 (M+Na)+.

Workup

  1. additiona catalytic amount of PEG-400 was added at rt
  2. filtrationThe solution was filtered
  3. washthe solids were washed with acetone
  4. customAcetone was evaporated under reduced pressure
  5. customthe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-d3a10c8500de435088b9910fb45d4ea1
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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