Reaction #792156

Reaction equation

2-amino-3-methylbenzoic acid

trichloromethyl chloroformate

→

off-white solid

8-Methyl-2H-3,1-benzoxazine-2,4(1H)-dione

Solvents

1,4-dioxane

1,4-dioxane

Conditions

Workup

1. 1
   Otherthe reaction temperature below 25° C
2. 2
   Otherto form during the addition
3. 3
   OtherThe precipitated solids were removed by filtration
4. 4
   Washwashed with 1,4-dioxane (2×20 mL) and hexane (2×15 mL)
5. 5
   Otherair-dried

Procedure

To a solution of 2-amino-3-methylbenzoic acid (6 g) in dry 1,4-dioxane (50 mL) was added dropwise a solution of trichloromethyl chloroformate (8 mL) in dry 1,4-dioxane (25 mL), with ice-water cooling to keep the reaction temperature below 25° C. A white precipitate began to form during the addition. The reaction mixture was stirred at room temperature overnight. The precipitated solids were removed by filtration and washed with 1,4-dioxane (2×20 mL) and hexane (2×15 mL) and air-dried to yield 6.51 g of off-white solid.

Source