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

HRID 1011464Notes

Reaction equation

HRID 1011464 reaction equation
Br[CH2:2][C:3]([NH:5][CH2:6][C:7]#[CH:8])=[O:4].[N+:9]([C:12]1[N:13](CC#C)[CH:14]=[CH:15][N:16]=1)([O-:11])=[O:10].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[N+:9]([C:12]1[N:13]([CH2:2][C:3]([NH:5][CH2:6][C:7]#[CH:8])=[O:4])[CH:14]=[CH:15][N:16]=1)([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 111596172-bromo-N-(prop-2-yn-1-yl)acetamideHCID 546751432-Nitro-1-(prop-2-ynyl)-1H-imidazole

Product 1

HCID 102199322-(2-Nitro-1H-imidazol-1-yl)-N-(prop-2-ynyl)acetamideYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

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).

Workup

  1. filtrationthe resultant precipitate (1.2 g) was filtered off
  2. washwashed with water (2×40 mL)
  3. extractionThe aqueous layer was extracted into EtOAc
  4. concentrationThe organic layer was concentrated to dryness
  5. customThe material was purified on a silica gel cartridge

Sources & evidence

ORD record
ord-5574b19a062f454fb924c4f558b699ac
Source dataset
uspto-grants-2011_07
Patent number
US07977361B2

Reaction notes

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