تفاعل #409988

معادلة التفاعل

3-(2-benzylthiothiazol-5-ylmethyl)-5-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine

dichloromethane

Javelle water

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title compound

3-(2-Chlorothiazol-5-ylmethyl)-5-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine

المذيبات

hydrochloric acid

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONare added dropwise
2. 2
   workup.STIRRINGAfter stirring for a further 30 minutes
3. 3
   أخرىthe organic phase is separated off
4. 4
   استخلاصthe aqueous phase is extracted repeatedly with a little dichloromethane
5. 5
   تجفيفthe combined organic phases are subsequently dried with sodium sulphate
6. 6
   أخرىevaporated under reduced pressure
7. 7
   workup.DISSOLUTIONThe oily residue is dissolved in tetrahydrofuran
8. 8
   أخرىprecipitated with hexane, whereby the product deposits on the walls of the vessel as a sticky material
9. 9
   أخرىThe solvent is decanted
10. 10
    workup.DISSOLUTIONthe residue is redissolved in tetrahydrofuran
11. 11
    تركيزthe solution is slowly concentrated

الإجراء التجريبي

2 g of 3-(2-benzylthiothiazol-5-ylmethyl)-5-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine are dissolved in a mixture of 10 ml of 4N aqueous hydrochloric acid, 20 g of ice and 30 ml of dichloromethane, and 30 g of Javelle water are added dropwise with stirring to the solution. After stirring for a further 30 minutes, the organic phase is separated off, the aqueous phase is extracted repeatedly with a little dichloromethane, and the combined organic phases are subsequently dried with sodium sulphate and evaporated under reduced pressure. The oily residue is dissolved in tetrahydrofuran and precipitated with hexane, whereby the product deposits on the walls of the vessel as a sticky material. The solvent is decanted, the residue is redissolved in tetrahydrofuran, and the solution is slowly concentrated, yielding 0.84 g of the title compound in the form of a semi-crystalline resin. A sample of this resin is purified by chromatography [silica gel; dichloromethane/methanol (95:5)], yielding crystals melting at 132 to 135°.

المصدر