Methyl iodide → Methyl 3-[5-(2,4-dichlorophenoxy)-2-nitrophenyl]tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

HRID 1451172Notes

Reaction equation

HRID 1451172 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[Cl:9][C:10]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:33]([O-:35])=[O:34])=[C:17]([N:19]2[C:24](=[O:25])[NH:23][C:22](=[O:26])[N:21]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[C:20]2=[O:32])[CH:18]=1.[Cl-].[NH4+]>CN(C)C=O>[Cl:9][C:10]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:33]([O-:35])=[O:34])=[C:17]([N:19]2[C:24](=[O:25])[N:23]([CH3:3])[C:22](=[O:26])[N:21]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[C:20]2=[O:32])[CH:18]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 11733582methyl 3-[5-(2,4-dichlorophenoxy)-2-nitrophenyl]tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate

Product 1

HCID 57155135Methyl 3-[5-(2,4-dichlorophenoxy)-2-nitrophenyl]tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (0.15 mL, 2.41 mmol) and potassium carbonate (0.19 g, 1.34 mmol) are added to a solution of methyl 3-[5-(2,4-dichlorophenoxy)-2-nitrophenyl]tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate (0.40 g, 0.83 mmol) in N,N-dimethylformamide. The reaction mixture is stirred overnight at room temperature and poured into a saturated ammonium chloride solution. The aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a yellow oil. Column chromatography of the oil using silica gel and an ethyl acetate/hexanes (1:3) solution gives the title product as a yellow foam which is identified by NMR spectral analysis.

Workup

  1. extractionThe aqueous mixture is extracted with ethyl acetate
  2. washwashed sequentially with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a yellow oil

Sources & evidence

ORD record
ord-2078bab0c8164aae962c01b5932aa14f
Source dataset
uspto-grants-1997_02
Patent number
US05604180

Reaction notes

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