تفاعل #4783

معادلة التفاعل

6-methyl-4-(3-nitrophenyl)-2-phenyl-5-thioureidomethylpyrimidine

methyl iodide

N,N-dimethylformamide

→

5-(1-imidazolin-2-ylaminomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter evaporating the solvent in vacuo
2. 2
   workup.DISSOLUTIONthe residual product was dissolved in ethanol (14 ml)
3. 3
   workup.ADDITIONEthylenediamine (0.33 g) was added
4. 4
   درجة الحرارةrefluxed for 2 hours
5. 5
   درجة الحرارةAfter cooling
6. 6
   workup.ADDITIONthe reaction mixture was poured into a mixture of chloroform (50 ml) and water (100 ml)
7. 7
   أخرىThe organic layer was separated
8. 8
   غسيلwashed with saturated aqueous sodium chloride
9. 9
   تجفيفdried over magnesium sulfate
10. 10
    أخرىevaporated in vacuo
11. 11
    workup.ADDITIONThe residual product was subjected to column chromatography on alumina eluting with a mixture of chloroform and methanol (50:1)
12. 12
    workup.ADDITIONThe fractions containing the object compound
13. 13
    تركيزconcentrated in vacuo
14. 14
    أخرىThe residue was recrystallized from ethanol

الإجراء التجريبي

A mixture of 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-thioureidomethylpyrimidine (0.7 g) and methyl iodide (0.31 g) in N,N-dimethylformamide (20 ml) was stirred for 7 hours at a room temperature. After evaporating the solvent in vacuo, the residual product was dissolved in ethanol (14 ml). Ethylenediamine (0.33 g) was added thereto and refluxed for 2 hours. After cooling, the reaction mixture was poured into a mixture of chloroform (50 ml) and water (100 ml), and adjusted pH to 11.0 with 10% aqueous potassium carbonate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, evaporated in vacuo. The residual product was subjected to column chromatography on alumina eluting with a mixture of chloroform and methanol (50:1). The fractions containing the object compound were combined and concentrated in vacuo. The residue was recrystallized from ethanol to give 5-(1-imidazolin-2-ylaminomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.06 g).

المصدر