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

HRID 1466991Notes

Reaction equation

HRID 1466991 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-f1d90c25d22c4bf3bafd9b524d8fcc8c
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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