Acetyl chloride → 6-Isopropyl-1H-benzo[d][1,3]oxazine-2,4-dione

Reaktionsgleichung

[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:13])[CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:15](OCC)=[O:16].C(Cl)(=O)C>O1CCOCC1>[CH: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]=1)([CH3:13])[CH3:12]

Komponenten

Versuchsvorschrift

A mixture of 2-amino-5-isopropylbenzoic acid (30. g, 16.7 mmol) and ethyl chloroformate (1.75 mL, 18.4 mmol) in dioxane (20 mL) was heated under reflux for 2 h. After cooling, acetyl chloride (1.4 mL) was added and heating under reflux continued for another 3 h. After cooling, the mixture was evaporated and the resulting solid digested with tert-butyl methyl ether: heptane (1:1, 20 mL) by heating under reflux for 1 h. The soild was then filtered off and washed with tert-butyl methyl ether: heptane (1:1, 10 mL). Yield 3.1 g (89%). m/z 204 (M—H−).