Potassium Carbonate → Diethyl 1-hexyl-2,5-dioxo-4-imidazolylphosphonate

HRID 1648512Notes

Reaction equation

HRID 1648512 reaction equation
[O:1]=[C:2]1[N:6]=[C:5]([P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])[C:4](=[O:15])[NH:3]1.C([O-])([O-])=O.[K+].[K+].I[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CN(C=O)C.CCOCC>[CH2:23]([N:3]1[C:4](=[O:15])[C:5]([P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[N:6][C:2]1=[O:1])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 125271-IodohexaneHCID 53733419Diethyl (2,5-dioxo-2,5-dihydro-1H-imidazol-4-yl)phosphonate

Product 1

HCID 53646860Diethyl 1-hexyl-2,5-dioxo-4-imidazolylphosphonate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of diethyl 2,5-dioxo-4-imidazolylphosphonate (6.00 g, 0.025 moles) in DMF (15 mL), under N2, is added K2CO3 (17.5g, 0.127 moles) and 1-iodohexane (3.75 mL, 0.025 moles). This mixture is stirred at room temperature for 16 hours. The mixture is diluted with ether (300 mL) and washed with water and brine and then dried over MgSO4. Evaporation of solvents under high vacuum affords the required product as a viscous yellow oil. (Mass spectrometry also revealed a small amount of diethyl 1,3-dihexyl-2,5-dioxo-4-imidazolylphosphonate) MS (EI) 321

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. customEvaporation of solvents under high vacuum

Sources & evidence

ORD record
ord-f154442dadb24ac08901a1f58bdbd0df
Source dataset
uspto-grants-1995_07
Patent number
US05436260

Reaction notes

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