تفاعل #1581

ord-1b12023f2a354fce9ed4c6252aa46b2d

معادلة التفاعل

O=C1C2=C(CCCC2)C(=O)N1c1ccc(Cl)cc1F
N-(4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide
O=[N+]([O-])O
nitric acid
O=C1C2=C(CCCC2)C(=O)N1c1cc([N+](=O)[O-])c(Cl)cc1F
title product
المردود 101.6%
O=C1C2=C(CCCC2)C(=O)N1c1cc([N+](=O)[O-])c(Cl)cc1F
N-(4-Chloro-2-fluoro-5-nitrophenyl)-1-cyclohexene-1,2-dicarboximide
المردود 101.6%

المذيبات

ظروف التفاعل

درجة الحرارة
-3°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةwhile maintaining the temperature at 0°-2° C.
  2. 2
    workup.ADDITIONpoured onto ice
  3. 3
    workup.STIRRINGThe aqueous mixture is stirred for several minutes
  4. 4
    ترشيحfiltered
  5. 5
    أخرىto obtain a solid which
  6. 6
    غسيلis washed with water
  7. 7
    أخرىdried

الإجراء التجريبي

A mixture of N-(4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide (24.4 g, 86.7 mmol) in sulfuric acid (150 mL) is cooled to -3° C., treated dropwise with nitric acid (70% real, 6.70 mL, 104 mmol) while maintaining the temperature at 0°-2° C., stirred at room temperature for 90 minutes, and poured onto ice. The aqueous mixture is stirred for several minutes, and filtered to obtain a solid which is washed with water and dried to give the title product as a white powder (28.6 g, mp 152°-155° C.).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05726126uspto-grants-1998_03