m-Chloroperbenzoic acid → 2-(Methanesulfinyl)[1,2,4]triazino[1,6-a]indole

HRID 1261976Notes

Reaction equation

HRID 1261976 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][S:13][C:14]1[N:26]=[CH:25][C:17]2=[CH:18][C:19]3[C:24]([N:16]2[N:15]=1)=[CH:23][CH:22]=[CH:21][CH:20]=3.C([O-])(O)=O.[Na+]>ClCCl.O>[CH3:12][S:13]([C:14]1[N:26]=[CH:25][C:17]2=[CH:18][C:19]3[C:24]([N:16]2[N:15]=1)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:9]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 574160742-(Methylsulfanyl)[1,2,4]triazino[1,6-a]indole

Product 1

HCID 574161002-(Methanesulfinyl)[1,2,4]triazino[1,6-a]indoleYield 98.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

261 g) Into a round-bottom flask, m-chloroperbenzoic acid (77% by weight in benzoic acid, 853 mg, 3.80 mmol) was added to a solution of 2-methylsulfanyl-[1,2,4]triazino[1,6-a]indole (780 mg, 3.60 mmol) in dichloromethane (20 mL), at 0° C. The reaction was stirred for 1 hour at room temperature. Saturated NaHCO3 in water was added and the reaction mixture was stirred for 30 minutes. The organic phase was separated, washed with brine, and dried over magnesium sulfate, then filtered. The solvent was removed under vacuum to afford 2-methanesulfinyl-[1,2,4]triazino[1,6-a]indole (820 mg, 98%) as an orange solid, which was used without further purification. 1H-NMR (CDCl3) δ 9.28 (s, 1H), 8.34 (d, J=8.5 Hz, 1H), 7.95 (d, J=8.1 Hz, 1H), 7.60 (m, 1H), 7.52 (m, 1H), 7.21 (s, 1H), 3.06 (s, 3H); LC/MS (ESI+): 254.5 (M+Na).

Workup

  1. stirringthe reaction mixture was stirred for 30 minutes
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-389644e5e5de43009ee35e2123ef7e15
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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