تفاعل #1244271

ord-9b99331a26a94464b68b74bc370e9dda

معادلة التفاعل

C#CCNC(=O)CBr
alkyne
C#CCNC(=O)CBr
2-Bromo-N-(prop-2-ynyl)acetamide
C#CCn1ccnc1[N+](=O)[O-]
2-nitroimidazole
C#CCn1ccnc1[N+](=O)[O-]
2-Nitro-1-(prop-2-ynyl)-1H-imidazole
O=C([O-])[O-].[K+].[K+]
K2CO3
C#CCNC(=O)Cn1ccnc1[N+](=O)[O-]
white solid
المردود 18.0%
C#CCNC(=O)Cn1ccnc1[N+](=O)[O-]
2-(2-Nitro-1H-imidazol-1-yl)-N-(prop-2-ynyl)acetamide
المردود 18.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحthe resultant precipitate (1.2 g) was filtered off
  2. 2
    غسيلwashed with water (2×40 mL)
  3. 3
    استخلاصThe aqueous layer was extracted into EtOAc
  4. 4
    تركيزThe organic layer was concentrated to dryness
  5. 5
    أخرىThe material was purified on a silica gel cartridge

الإجراء التجريبي

To a round bottom flask was added alkyne 18 (1.56 g, 8.84 mmol), 2-nitroimidazole 10 (1 g, 8.84 mmol) and K2CO3 (1.22 g, 8.84 mmol) in DMF (10 mL). The reaction was stirred overnight. The reaction was diluted with water (100 mL) and the resultant precipitate (1.2 g) was filtered off and washed with water (2×40 mL). The aqueous layer was extracted into EtOAc. The organic layer was concentrated to dryness and combined with the precipitate. The material was purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford a 19 white solid (324 mg, 18%). Mass Spec (lo-res): Calc'd for C8H8N4O3: 208.06; found: 209.10 (M+H).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07807394B2uspto-grants-2010_10