Dimethyl Sulfoxide → HCID 59506362, compound

HRID 1798895Notes

Reaction equation

HRID 1798895 reaction equation
C([N:8]1[C:18]2=[C:19]3[C:14]([N:15]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)[CH2:16][CH2:17]2)=[N:13]C(SC)=[N:11][C:10]3=[N:9]1)C1C=CC=CC=1.[CH:31]1[CH:36]=[C:35](Cl)[CH:34]=[C:33]([C:38](OO)=O)[CH:32]=1.[CH3:42][S:43]([CH3:45])=[O:44].C([O-])(O)=[O:47].[Na+]>ClCCl>[CH2:38]([N:9]1[C:10]2=[C:19]3[C:14](=[N:13][C:42]([S:43]([CH3:45])(=[O:47])=[O:44])=[N:11]2)[N:15]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[CH2:16][CH2:17][C:18]3=[N:8]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59506459HCID 59506459, compound

Product 1

HCID 59506362HCID 59506362, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1-benzyl-6-(4-methoxybenzyl)-4-(methylthio)-1,6,7,8-tetrahydro-1,2,3,5,6-pentaazaacenaphthylene (2.00 g, 4.79 mmol) in dichloromethane (40 mL) was added MCPBA (3.62 g, 50%, 10.53 mmol) and the mixture was stirred overnight. DMSO (5 mL) was added and the mixture was stirred for 10 min to quench the reaction. Saturated aqueous NaHCO3 (150 mL) and dichloromethane (250 mL) was added and the mixture was stirred for 1-2 h. dichloromethane layer was separated and washed with aqueous NaCl (3×150 mL), dried over Na2SO4, Filtered and concentrated to give the crude product as a brown solid (1.66 g, 77%). The crude product was used for next step directly without further purification. LC-Mass (m/e): 450.52 (M+1).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. customto quench
  3. customthe reaction
  4. customwas separated
  5. washwashed with aqueous NaCl (3×150 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationFiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-82798c816e6e4e729434b7d8729666c4
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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