Methyl iodide → 5-Chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 889609Notes

Reaction equation

HRID 889609 reaction equation
[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[O:9][C:8](=[O:13])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:16]I>CN(C)C=O>[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[O:9][C:8](=[O:13])[N:7]([CH3:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6390585-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 5867555-Chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an atmosphere of nitrogen, 5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (10 g, 50.61 mmol, 1.00 equiv) was dissolved in N,N-dimethylformamide (100 ml) at about 5° C. Sodium hydride (2.8 g, 121.5 mmol, 2.4 equiv) and methyl iodide (5.7 ml, 2 equiv) were then added, and the resulting mixture was stirred at ambient temperature for about 16 hours. The mixture was purged with nitrogen for about 1 hour to give the title product as a yellow solid, which was used directly in the next step without any purification.

Workup

  1. customThe mixture was purged with nitrogen for about 1 hour

Sources & evidence

ORD record
ord-e7e4e9b8047747d0af106004aa2bed66
Source dataset
uspto-grants-2012_08
Patent number
US08252933B2

Reaction notes

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