Allyl iodide → 7-Fluoro-1-(2-propen-1-yl)-2H-3,1-benzoxazine-2,4(1H)-dione

HRID 657118Notes

Reaction equation

HRID 657118 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])[O:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.[H-].[Na+].[CH2:16](I)[CH:17]=[CH2:18]>CN(C=O)C.O>[F:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])[O:7][C:8](=[O:10])[N:9]([CH2:18][CH:17]=[CH2:16])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 100581387-Fluoroisatoic anhydride

Product 1

HCID 866353597-Fluoro-1-(2-propen-1-yl)-2H-3,1-benzoxazine-2,4(1H)-dioneYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-fluoro-2H-3,1-benzoxazine-2,4(1H)-dione (5.01 g, 27.7 mmol) in DMF (100 ml) at 0° C. was added sodium hydride (1.11 g, 27.7 mmol, 60% in paraffin) over 15 min. Allyl iodide (2.6 ml, 27.7 mmol) was added and the solution stirred for 2 h, then poured onto ice (100 g) in water (200 ml). The precipitate was collected, washed with water, then hexane and dried under vacuum at 40° C. to yield the title compound (4.53 g, 74%) as an off-white solid.

Workup

  1. customThe precipitate was collected
  2. washwashed with water
  3. dry with materialhexane and dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-3e4a7c1284434ab6a54e1c0a92a97f2e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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