反应 #2307988

反应方程式

sodium bicarbonate

sodium hydride

1,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine

tetrahydrofuranylmethyl triflate

hydrochloric acid

→

1-{(tetrahydro-3-furanyl)methyl}-2-nitro-3-methylguanidine

溶剂

DMF

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was stirred at 50° C. for 2 hours
2. 2
   workup.STIRRINGby stirring at 50° C. for 2 hours
3. 3
   萃取extracted with dichloromethane
4. 4
   其他the extract was dried
5. 5
   浓缩concentrated
6. 6
   其他The residue thus obtained
7. 7
   其他was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1)

实验过程

A mixture comprising 10.0 g of (tetrahydro-3-furanyl)methanol, 29.5 g of trifluoromethanesulfonic anhydride, 10.0 g of pyridine and 200 ml of dichloromethane was stirred for an hour at room temperature. Water was poured into the reaction solution to separate the organic layer, which was washed with 1 N hydrochloric acid, water and a saturated saline solution, dried, and concentrated to obtain 20 g of 3-tetrahydro-furanylmethyl triflate. 3.25 g of 60% sodium hydride were added to 12.5 g of 1,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine and 60 ml of DMF at room temperature, followed by stirring for an hour. 20.0 g of the 3 tetrahydrofuranylmethyl triflate were added thereto, and the mixture was stirred at 50° C. for 2 hours. After cooling the mixture to room temperature, 50 ml of 2N hydrochloric acid were added thereto, followed by stirring at 50° C. for 2 hours. The resultant mixture was neutralized with sodium bicarbonate and extracted with dichloromethane, and the extract was dried and concentrated. The residue thus obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1) to obtain 7.8 g of 1-{(tetrahydro-3-furanyl)methyl}-2-nitro-3-methylguanidine (dinotefuran).

来源