Reaction #6456

Reaction equation

5,5-dimethyl-1,3-cyclohexanedione

triethylamine

benzothiadiazole-7-carboxylic acid chloride

→

title compound

Yield 87.5%

3-(benzo-1,2,3-thiadiazole-7-carbonyloxy)-5,5-dimethyl-cyclohex-2-enone

Yield 87.5%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   WashThe ethyl acetate solution is washed with H2O
2. 2
   Otherdried
3. 3
   Concentrationconcentrated
4. 4
   OtherPurification by column chromatography

Procedure

5.6 g (0.04 mol) of 5,5-dimethyl-1,3-cyclohexanedione are dissolved in a mixture of 4.4 g (0.044 mol) of triethylamine and 120 ml of ethyl acetate. 8.7 g (0.044 mol) of benzothiadiazole-7-carboxylic acid chloride are added dropwise at 15° to 20° C., and the mixture is subsequently stirred overnight at room temperature. The ethyl acetate solution is washed with H2O, dried and concentrated. Purification by column chromatography using ethyl acetate/hexane gives 10.5 g (87.5%) of the title compound, melting point 131°-133° C.

Source