Potassium Carbonate → HCID 22288686, compound

HRID 1768114Notes

Reaction equation

HRID 1768114 reaction equation
S(O)(O)(=O)=O.[NH2:6][C:7]1[NH:8][CH:9]=[CH:10][N:11]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.O.C1OCCOCCOCCOCCOCCOC1>[CH:14]1[C:13]([N:8]2[C:7]([NH2:6])=[N:11][CH:10]=[CH:9]2)=[CH:18][CH:17]=[C:16]([N+:19]([O-:21])=[O:20])[CH:15]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 114661-Bromo-4-nitrobenzeneHCID 135136Bis(2-amino-1H-imidazole) sulphate

Product 1

HCID 22288686HCID 22288686, compoundYield 98%

Reagents, catalysts & solvents 4

HCID 2855718-Crown-6CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-aminoimidazole sulfate (2.24 g, 17 mmol) in DMF (30 mL) was added 4-bromo-1-nitrobenzene (3.4 g, 17 mmol), K2CO3 (4.69 g, 34 mmol) and 18-crown-6 (50 mg), and the resulting mixture was stirred at 80° C. for 16 hours. The mixture was cooled to room temperature, and was diluted with EtOAc (150 mL) and water (50 mL). The organic layer was washed with brine (20 mL×5), dried over MgSO4, and concentrated to give 4-(2′-amino-imidazol-1′-yl)nitrobenzene (3.23 g, 98%). 1H NMR (CD3OD) δ 8.38 (d, J=9.1 Hz, 2H), 7.73 (d, J=9.1 Hz, 2H), 6.90 (d, J=1.9 Hz, 1H), 6.66 (d, J=1.9 Hz, 1H); MS(ES+) m/z 205 (M+H, 100).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washThe organic layer was washed with brine (20 mL×5)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d9cbc039b60d405a8fb46fa808b90499
Source dataset
uspto-grants-2007_06
Patent number
US07235575B2

Reaction notes

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