Water → HCID 23509600, compound

HRID 1278680Notes

Reaction equation

HRID 1278680 reaction equation
[CH3:1][C:2]1([CH3:18])[O:7][C:6](=[O:8])[NH:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]3[NH:14][CH:15]=[CH:16][CH:17]=3)=[CH:12][C:3]1=2.[C:19](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH3:1][C:2]1([CH3:18])[O:7][C:6](=[O:8])[NH:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]3[N:14]([CH3:19])[CH:15]=[CH:16][CH:17]=3)=[CH:12][C:3]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 99647884,4-Dimethyl-6-(1H-pyrrol-2-yl)-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Product 1

HCID 23509600HCID 23509600, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 4,4-dimethyl-6-(1H-pyrrol-2-yl)-1,4-dihydro-benzo[d][1,3]oxazin-2-one (1.5 g, 6.2 mmol) in dimethylformamide (20 mL) at room temperature was added sequentially potassium carbonate (4.28 g, 31 mmol) and a solution of methyl iodide (1.16 mL, 19 mmol) in dimethylformamide (5 mL). After 1 h, the reaction mixture was boiled. The reaction was cooled to room temperature, poured into water (50 mL) and extracted with ethyl ether (2×50 mL). The organic layers were combined, washed with brine (30 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography on silica gel (40% ethyl acetate/hexane) gave the title compound as an off-white powder (0.5 g, 31%) mp 230° C. 1H NMR (CDCl3) δ1.71 (s, 6 H), 3.42 (s, 3 H), 6.31 (dd, 1 H, J=2.9, 5.9 Hz), 6.47 (m, 1 H), 6.88 (m, 1 H), 6.94 (d, 1 H, J=8.6 Hz), 7.26 (d, 1 H, J=2.2 Hz), 7.41 (dd, 1 H, J=2.2, 8.6 Hz), 8.43 (bs, 1 H). MS ((−) ESI) m/z 255 [M−H]−. Anal. Calcd for C15H16N2O2: C, 70.29; H, 6.29; N, 10.93. Found: C, 68.59; H, 6.16; N, 10.49.

Workup

  1. extractionextracted with ethyl ether (2×50 mL)
  2. washwashed with brine (30 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography on silica gel (40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-667f18ba4cb842879f4e2f6fe4c79890
Source dataset
uspto-grants-2002_09
Patent number
US06444668B1

Reaction notes

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