Dimethylformamide → HCID 59340108, compound

HRID 908550Notes

Reaction equation

HRID 908550 reaction equation
[H-].[Na+].[CH3:3]N(C)C=O.[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[O:18])[O:16][C:15](=[O:19])[NH:14][C:13]=2[CH:20]=1.IC>O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[O:18])[O:16][C:15](=[O:19])[N:14]([CH3:3])[C:13]=2[CH:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 115215774-Bromoisatoic anhydride

Product 1

HCID 59340108HCID 59340108, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.47 g, 12 mmol) was added to a 3 neck 250 mL RBF under nitrogen and then washed with hexanes. Once the hexanes were decanted, N,N-dimethylformamide (20.0 mL, 11 mmol) was added. The resulting mixture was cooled to 0° C. using an ice-water bath, and then 7-bromo-1H-benzo[d][1,3]oxazine-2,4-dione (2.7 g, 11 mmol) was added in one batch. After stirring at room temperature for 1 hour, iodomethane (0.70 mL, 11 mmol) was added dropwise to the yellow solution, and the reaction mixture was stirred for 16 hours. Water (50 mL) was added, and the resulting precipitate that formed was collected via filtration. The solid was washed with additional water (100 mL), followed by ether (100 mL). Drying in a vacuum oven overnight at 50° C. afforded the desired product as an off-white solid (2.1 g, 74% yield).

Workup

  1. washwashed with hexanes
  2. customOnce the hexanes were decanted
  3. stirringthe reaction mixture was stirred for 16 hours
  4. customthe resulting precipitate that formed
  5. filtrationwas collected via filtration
  6. washThe solid was washed with additional water (100 mL)
  7. customDrying in a vacuum oven overnight at 50° C.

Sources & evidence

ORD record
ord-aa92a657ef9c4d8c97f8ef0c702a42ad
Source dataset
uspto-grants-2011_09
Patent number
US08017626B2

Reaction notes

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