Methyl iodide → HCID 11223771, compound

HRID 1296519Notes

Reaction equation

HRID 1296519 reaction equation
[CH3:1][C:2]1([CH3:25])[C:7]2[CH:8]=[C:9]([O:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=3[Cl:23])(=[O:15])=[O:14])[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:24])[O:3]1.[C:26](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH3:26][N:5]1[C:6]2[CH:11]=[CH:10][C:9]([O:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=3[Cl:23])(=[O:15])=[O:14])=[CH:8][C:7]=2[C:2]([CH3:25])([CH3:1])[O:3][C:4]1=[O:24]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11246633HCID 11246633, compound

Product 1

HCID 11223771HCID 11223771, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-2,3-dichlorobenzenesulfonate (0.50 g, 1.24 mmol) in dimethylformamide (DMF) (6 mL) with potassium carbonate (0.51 g, 3.72 mmol) was added methyl iodide (0.1 mL, 1.60 mmol). After stirring overnight at room temperature, the solution was then quenched with ammonium chloride solution (sat.) and extracted several times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated. Trituration with ether gave (1,4,4-trimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-2,3-dichlorobenzenesulfonate as a white solid (0.30 g, 59%). 1H NMR (DMSO-d6): δ 8.14 (dd, J=8.1, 1.5 Hz, 1H), 7.92 (dd, J=8.1, 1.5 Hz, 1H), 7.61 (t, J=8.1 Hz, 1H), 7.12 (s, 2H), 7.00 (m, 1H), 3.25 (s, 3H), 1.49 (s, 6H). MS (ESI) m/z 416/418/420 ([M+H]+); Anal. calcd for C17H15Cl2NO5S: C, 49.05; H, 3.63; N, 3.36. Found: C, 49.01; H, 3.44; N, 3.15.

Workup

  1. customthe solution was then quenched with ammonium chloride solution (sat.)
  2. extractionextracted several times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ff282516b9fa480caa2636e838f3316c
Source dataset
uspto-grants-2007_07
Patent number
US07247625B2

Reaction notes

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