تفاعل #71474

ord-92c9590d2faa45dc85430e736fa96f66

معادلة التفاعل

ClCc1ccccc1
Benzyl chloride
O=[N+]([O-])c1ncc[nH]1
2-nitroimidazole
CCN(CC)CC
triethylamine
O=[N+]([O-])c1nccn1Cc1ccccc1
title compound
المردود 50.4%
O=[N+]([O-])c1nccn1Cc1ccccc1
1-Benzyl-2-nitro-1H-imidazole
المردود 50.4%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةat reflux for 72 h
  2. 2
    غسيلwashed with H2O and brine
  3. 3
    تجفيفdried (sodium sulfate)
  4. 4
    ترشيحfiltered
  5. 5
    تركيزconcentrated
  6. 6
    أخرىThe residue was purified by silica gel column chromatography (Hex/EtOAc, 7:3)

الإجراء التجريبي

Benzyl chloride (1.8 mL, 15.4 mmol, 1.2 equiv) was added to a solution of 2-nitroimidazole (1.45 g, 12.8 mmol) and triethylamine (3.6 mL, 25.7 mmol, 2 equiv) in DCM (40 mL). The reaction mixture was stirred at reflux for 72 h, allowed to cool to rt, diluted with DCM, washed with H2O and brine, dried (sodium sulfate), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 7:3) to afford 1.31 g of the title compound as a white solid: ES-MS: 204.0 [M+H]+; tR=3.72 min (System 1); TLC: Rf=0.22 (Hex/EtOAc, 7:3).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08536175B2uspto-grants-2013_09