Diethyl Ether → 5-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 2169843Notes

Reaction equation

HRID 2169843 reaction equation
[C:1](Cl)(=O)[O:2]C(Cl)(Cl)Cl.[NH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:11]=1[C:12]([OH:14])=[O:13].C(OCC)C>O1CCOCC1>[CH3:19][C:15]1[C:11]2[C:12](=[O:14])[O:13][C:1](=[O:2])[NH:9][C:10]=2[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10426DiphosgeneHCID 1512106-Methylanthranilic acid

Product 1

HCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneYield 56%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Trichloromethyl carbonochloridate (2.04 mL, 16.9 mmol) was added to 2-amino-6-methylbenzoic acid (2.13 g, 14.1 mmol) in anhydrous dioxane (32 mL) under nitrogen, then refluxed for 30 minutes. Diethyl ether (100 mL) was added, and the precipitated solid was collected by filtration to give 5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione (1.4 g, 56%) which was used without further purification.

Workup

  1. temperaturerefluxed for 30 minutes
  2. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-82ba5f6219bd4142ad6feb89bf1b6ff5
Source dataset
uspto-grants-2015_06
Patent number
US09049878B2

Reaction notes

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