Methyl iodide → HCID 57671875, compound

HRID 1182772Notes

Reaction equation

HRID 1182772 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]([CH2:23][O:24][C:25]([C:27]2[S:28][C:29]([CH3:32])=[CH:30][CH:31]=2)=[O:26])=[C:21]2[C:16]([NH:17][C:18]([CH3:35])([CH3:34])[C:19](=[O:33])[NH:20]2)=[CH:15][CH:14]=1.CI.[C:38](=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]([CH2:23][O:24][C:25]([C:27]2[S:28][C:29]([CH3:32])=[CH:30][CH:31]=2)=[O:26])=[C:21]2[C:16]([NH:17][C:18]([CH3:35])([CH3:34])[C:19](=[O:33])[N:20]2[CH3:38])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 57671771HCID 57671771, compound

Product 1

HCID 57671875HCID 57671875, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-(2-methoxy-4-methoxymethoxyphenyl)-8-(5-methylthiophen-2-ylcarbonyloxymethyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 11, 1.58 g, 3.18 mmol), methyl iodide (400 μL, 6.43 mmol), and cesium carbonate (2.24 g, 6.87 mmol) was suspended in anhydrous N,N-dimethylformamide (30 mL) and stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate (150 mL), washed with water (150 mL) and saturated brine (150 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (1.38 g) as a pale yellow amorphous product. (Yield 85%)

Workup

  1. washwashed with water (150 mL) and saturated brine (150 mL) successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-ccba7c9b3a0e4510a4b060005f08f453
Source dataset
uspto-grants-2014_03
Patent number
US08664221B2

Reaction notes

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