Reaction #1244271

Reaction equation

alkyne

2-Bromo-N-(prop-2-ynyl)acetamide

2-nitroimidazole

2-Nitro-1-(prop-2-ynyl)-1H-imidazole

K2CO3

→

white solid

Yield 18.0%

2-(2-Nitro-1H-imidazol-1-yl)-N-(prop-2-ynyl)acetamide

Yield 18.0%

Solvents

DMF

water

Conditions

Workup

1. 1
   Filtrationthe resultant precipitate (1.2 g) was filtered off
2. 2
   Washwashed with water (2×40 mL)
3. 3
   ExtractionThe aqueous layer was extracted into EtOAc
4. 4
   ConcentrationThe organic layer was concentrated to dryness
5. 5
   OtherThe material was purified on a silica gel cartridge

Procedure

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).

Source