تفاعل #3156

معادلة التفاعل

sodium methylate

5-amidino-2-methylcoumaran hydrochloride

product

5-carboxy-2-methylcoumaran

→

(-2methylcoumaran-5-yl)-5-(4-octylphenyl)pyrimidine

المردود 58.4%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed for 5 hours and 10 minutes
2. 2
   أخرىAfter the reaction
3. 3
   درجة الحرارةthe reaction mixture was cooled on an ice-common salt bath
4. 4
   أخرىto precipitate a crystal
5. 5
   ترشيحThe crystal was recovered by filtration
6. 6
   غسيلby washing with water
7. 7
   workup.DISSOLUTIONThe resultant crystal was dissolved in toluene
8. 8
   تجفيفdried with mirabilite
9. 9
   workup.DISTILLATIONAfter distilling-off of the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent:toluene/ethyl acetate=100/1)
10. 10
    أخرىrecrystallized from a mixture solvent of toluene and methanol

الإجراء التجريبي

0.40 g (1.88 mM) of 5-amidino-2-methylcoumaran hydrochloride (M5) as an intermediate product prepared in Example 1, 0.79 g (1.90 mM) of 3-dimethylamino-2-(4-octylphenyl)-N,N-dimethylpropene-(2)-ammonium perchlorate 0.41 g (7.59 mM) of sodium methylate and 15 ml of methanol were placed in a 50 ml-round bottomed flask and refluxed for 5 hours and 10 minutes under stirring. After the reaction, the reaction mixture was cooled on an ice-common salt bath to precipitate a crystal. The crystal was recovered by filtration, followed by washing with water. The resultant crystal was dissolved in toluene and dried with mirabilite. After distilling-off of the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent:toluene/ethyl acetate=100/1) and recrystallized from a mixture solvent of toluene and methanol to obtain 0.44 of 2 (-2methylcoumaran-5-yl)-5-(4-octylphenyl)pyrimidine (Ex. Comp. No. I-235) (Yield: 58.4%). The product showed the following phase transition temperatures (°C.). ##STR92##

المصدر