Methyl iodide → HCID 86690004, compound

HRID 1186733Notes

Reaction equation

HRID 1186733 reaction equation
O=[C:2]1[NH:11][C:10]2[C:9]3[CH2:12][CH2:13][CH2:14][CH2:15][C:8]=3[CH:7]=[CH:6][C:5]=2[N:4]([C:16]2[CH:17]=[C:18]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N+:32]([O-:34])=[O:33])(=[O:25])=[O:24])[CH:19]=[CH:20][CH:21]=2)C1=O.[CH3:36]I.[C:38](=[O:41])([O-])[O-].[K+].[K+].[C:44](=[O:47])([O-])O.[Na+]>C(Cl)(Cl)Cl.CN(C=O)C>[CH3:36][N:22]([C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([N:4]2[C:5]3[CH:6]=[CH:7][C:8]4[CH2:15][CH2:14][CH2:13][CH2:12][C:9]=4[C:10]=3[N:11]([CH3:2])[C:44](=[O:47])[C:38]2=[O:41])[CH:17]=1)[S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N+:32]([O-:34])=[O:33])(=[O:24])=[O:25]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86690003HCID 86690003, compound

Product 1

HCID 86690004HCID 86690004, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[3-(2,3-dioxo-2,3,7,8,9,10-hexahydrobenzo[f]quinoxalin-4(1H)-yl)phenyl]-2-nitrobenzenesulfonamide (100 mg, 0.203 mmol), methyl iodide (35 mg, 0.244 mmol), potassium carbonate (30.9 mg, 0.223 mmol), and dry DMF (2 mL) was stirred at room temperature for 18 hours. To the reaction solution were added ice-cold water and a saturated aqueous sodium hydrogen carbonate solution. The precipitated crystal was collected by filtration, washed with water, and dried. The obtained crude compound was subjected to silica gel column chromatography (chloroform) to obtain N-methyl-N-[3-(1-methyl-2,3-dioxo-2,3,7,8,9,10-hexahydrobenzo[f]quinoxalin-4(1H)-yl)phenyl]-2-nitrobenzenesulfonamide (70 mg, yield 66%) from the formerly eluted fraction.

Workup

  1. additionTo the reaction solution were added ice-cold water
  2. filtrationThe precipitated crystal was collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe obtained crude compound

Sources & evidence

ORD record
ord-73c7cf168f0e453bbd58c734f20d0470
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

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