Реакция #168890

Уравнение реакции

2-chloro-4-(phenylthio)pyrimidine

diisopropylethylamine

1,3-phenylenediamine

→

product

Выход 42.0%

N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine

Выход 42.0%

Растворители

2-ethoxyethanol

ethyl acetate

Условия реакции

Обработка

1. 1
   ТемператураThe whole was heated
2. 2
   Температураunder reflux for 20 hours
3. 3
   Промывкаwashed with water and brine
4. 4
   СушкаThe organic solution was dried (Na2SO4)
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   Другоеchromatographed on silica gel

Методика

To a stirred mixture of 2-chloro-4-(phenylthio)pyrimidine (300 mg, 1.35 mmol) and diisopropylethylamine (0.35 mL, 2.02 mmol) in 2-ethoxyethanol (2 mL), was added 1,3-phenylenediamine (291 mg, 2.70 mmol) in one portion. The whole was heated under reflux for 20 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (20 mL), washed with water and brine. The organic solution was dried (Na2SO4), concentrated in vacuo. The residue was flash chromatographed on silica gel using ethyl acetate:petroleum ether (20:80→0:50) as eluant to give the product (167 mg, 42%).

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