Реакция #1671838

ord-4fb762a2e3904d59ab7ae167953b0f9c

Уравнение реакции

O
water
O=c1[nH]cc(-c2ccccc2)[nH]1
4-Phenyl-2,3-dihydro-1H-2-imidazolone
[H-].[Na+]
sodium hydride
O=C(N1CCc2cc(S(=O)(=O)Cl)ccc21)C(F)(F)F
N-trifluoroacetyl-indoline-5-sulfonylchloride
O=C(N1CCc2cc(S(=O)(=O)n3cc(-c4ccccc4)[nH]c3=O)ccc21)C(F)(F)F
4-phenyl-1-(N-trifluoroacetylindoline-5-sulfonyl)-2-imidazolone
Выход 70.0%

Растворители

Условия реакции

Температура
0°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеprepared in Preparation 2
  2. 2
    workup.STIRRINGThe reaction mixture was stirred at room temperature for 4 hours
  3. 3
    Температураcooled down again to 0° C.
  4. 4
    Другоеwas formed
  5. 5
    ДругоеThe resulting precipitate was collected
  6. 6
    Промывкаwashed with water
  7. 7
    Другоеdried

Методика

4-Phenyl-2,3-dihydro-1H-2-imidazolone (4 g, 24.84 mmol) prepared in Preparation 1 was suspended in 30 ml of dimethylformamide and cooled down to 0 ° C. After sodium hydride (60% oily, 1.09 g, 27.3 mmol) was added thereto, the resulting mixture was stirred for a few minutes at 0° C. until it became a clear solution. To the reaction mixture was added portionwise at 0° C. the N-trifluoroacetyl-indoline-5-sulfonylchloride (8.56 g, 27.32 mmol) prepared in Preparation 2. The reaction mixture was stirred at room temperature for 4 hours, cooled down again to 0° C., and then water was slowly added to the mixture until precipitate was formed. The resulting precipitate was collected, washed with water, and dried to afford 7.6 g of 4-phenyl-1-(N-trifluoroacetylindoline-5-sulfonyl)-2-imidazolone.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05932742uspto-grants-1999_08