Diethyl Ether → 8-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 1186090Notes

Reaction equation

HRID 1186090 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.C(OCC)C>O1CCCC1>[CH3:12][O:11][C:10]1[C:2]2[NH:1][C:14](=[O:16])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 94429TriphosgeneHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 105596798-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dioneYield 226.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-amino-3-methoxybenzoic acid (5 g, 30 mmol) in anhydrous tetrahydrofuran (50 mL) was added triphosgene (3.55 g, 12 mmol). This mixture was heated to reflux under a nitrogen atmosphere for 3 hours. It was cooled to ambient temperature, and diethyl ether (50 mL) was added. The mixture was filtered to yield 8-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione (5.25 g, 91%) as a solid.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere for 3 hours
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-22411f010dba45a3aa7a2294d9f9f743
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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