Methyl iodide → 3-Methyl-6,7,8,9-tetrahydrobenzo[1,2-b]1, 2,3-triazino[4,5-d]selenophen-4-one

HRID 1097229Notes

Reaction equation

HRID 1097229 reaction equation
[N:1]1[C:6]2[C:7]3[CH2:13][CH2:12][CH2:11][CH2:10][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[CH2:10][CH2:11][CH2:12][CH2:13][C:7]=3[C:6]=2[N:1]=[N:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1361550736,7,8,9-tetrahydro-3H-benzo[1,2-b]1,2,3-triazino[4,5-d]selenophen-4-one

Product 1

HCID 595472073-Methyl-6,7,8,9-tetrahydrobenzo[1,2-b]1, 2,3-triazino[4,5-d]selenophen-4-oneYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 6,7,8,9-tetrahydro-3H-benzo[1,2-b]1,2,3-triazino[4,5-d]selenophen-4-one (450 mg, 1.76 mmol) in acetone (50 mL) was added sequentially potassium carbonate (480 mg, 3.52 mmol), iodomethane (0.13 mL, 2.11 mmol) and a catalytic amount of PEG-400 was added and stirred 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-ethyl acetate (90:10) as eluents to give the product as a pale yellow color solid (340 mg, 72%), which was recrystallized from chloroform-hexane (170 mg), mp 110-112° C. IR (neat) νmax 3438, 1668, 1220, 1018 cm−1; 1H NMR (400 MHz, CDCl3): δ 4.05 (3H, s, —NCH3), 2.94-2.96 (4H, m, H-6,9), 1.91-1.97 (4H, m, H-7,8); 13C NMR (100 MHz, CDCl3): δ 156.1, 155.1, 152.5, 133.9, 128.5, 37.4, 28.4, 24.8, 23.6, 21.4; LC-MS (positive ion mode): m/z 268, 270 (M+H)+.

Workup

  1. additiona catalytic amount of PEG-400 was added
  2. stirringthe mixture was stirred at rt for 16 h
  3. filtrationThe solution was filtered
  4. washthe solids were washed with acetone
  5. customAcetone was evaporated under reduced pressure
  6. customthe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-026812f821b94708aa358911691914cd
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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