تفاعل #216859

معادلة التفاعل

dimethylthiocarbamoyl chloride

sodium hydride

DMF

methyl 3-(1-adamantyl)-4-hydroxybenzoate

→

expected product

المردود 63.0%

methyl 3-(1-adamantyl)-4-(dimethylaminothiocarbonyloxy)benzoate

المردود 63.0%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThere are then added
2. 2
   استخلاصextracted with ethyl ether
3. 3
   أخرىThe organic phase is decanted
4. 4
   أخرىdried on magnesium sulfate
5. 5
   أخرىevaporated
6. 6
   أخرىThe resulting residue is purified by chromatography on a silica column
7. 7
   غسيلeluted with a 70:30 mixture of dichloromethane and hexane

الإجراء التجريبي

Into a round bottom flask, there are introduced 2.4 g (0.08 mole) of sodium hydride (80% in oil) and 250 ml of DMF. Under a nitrogen current, there are slowly added 22.9 g (0.08 g mole) of methyl 3-(1-adamantyl)-4-hydroxybenzoate. The mixture is stirred until the cessation of gaseous emission. There are then added, all at once, 12.9 g (0.104 mole) of dimethylthiocarbamoyl chloride and the mixture is stirred for 16 hours at ambient temperature. The reaction medium is poured into water and extracted with ethyl ether. The organic phase is decanted, dried on magnesium sulfate and evaporated. The resulting residue is purified by chromatography on a silica column eluted with a 70:30 mixture of dichloromethane and hexane. After evaporation of the solvents, 1.8 g (63% yield) of the expected product having a melting point of 174°-175° C. are recovered.

المصدر