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

HRID 1033112

Reaction equation

HRID 1033112 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 (17.5 g, 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).

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-e171d2619a6f4e12831c6f542031fa3d
Source dataset
uspto-grants-1994_05
Patent number
US05308853

Linked notes

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