Tetrahydrofuran → 6-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C1C[O:16][CH2:15]C1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:15](=[O:16])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-amino-5-methoxy-benzoic acid (1.2 g, 7 mmol) in anhydrous THF (50 mL) triethylamine (1.0 mL, 7 mmol) was added and the mixture was cooled down to 0° C. Then triphosgene (2.0 g, 7 mmol) was added portion wise and the reaction allowed to reach room temperature and left stirring for 18 hours. 1 mL of H2O was carefully added to the mixture and the solvent was removed under reduced pressure. The residue was precipitated from H2O, affording 1.3 g of the titled compound (96% yield).
Workup
- customto reach room temperature
- waitleft
- customthe solvent was removed under reduced pressure
- customThe residue was precipitated from H2O
Sources & evidence
- ORD record
- ord-7c7a062bdac74258ab0cac3740fa6835
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865704B2
Reaction notes
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