Phosphorus oxychloride → HCID 20780222, compound

HRID 1293083Notes

Reaction equation

HRID 1293083 reaction equation
FC(F)(F)C([O-])=O.[CH2:8]([O:10][C:11]([C:13]1[N:17]2[CH2:18][C:19](=O)[N:20]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[C:16]2=[NH+:15][C:14]=1[CH3:31])=[O:12])[CH3:9].P(Cl)(Cl)([Cl:34])=O>>[CH2:8]([O:10][C:11]([C:13]1[N:17]2[CH:18]=[C:19]([Cl:34])[N:20]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[C:16]2=[N:15][C:14]=1[CH3:31])=[O:12])[CH3:9]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469267HCID 178469267, compound

Product 1

HCID 20780222HCID 20780222, compound

Procedure

A solution of 3-ethoxycarbonyl-2-methyl-6-oxo-7-(2,4,6-trimethyl-phenyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazolium trifluoroacetate (22.2 mg, 0.050 mmol) in phosphorus oxychloride (1 mL) was heated at 150° C. for 48 h. The excess of phosphorus oxychloride was removed under reduced pressure, the residue was dissolved in saturated aqueous solution of sodium bicarbonate (20 mL) and extracted with ethyl acetate (5×20 mL). The combined organic extracts were dried with MgSO4. The solvent was removed under reduced pressure and the crude product was dried under pump vacuum overnight. Yield—23.3 mg (99%). LC/MS: tR=1.93 min., MS: [M+H]=346.

Workup

  1. customThe excess of phosphorus oxychloride was removed under reduced pressure
  2. dissolutionthe residue was dissolved in saturated aqueous solution of sodium bicarbonate (20 mL)
  3. extractionextracted with ethyl acetate (5×20 mL)
  4. dry with materialThe combined organic extracts were dried with MgSO4
  5. customThe solvent was removed under reduced pressure
  6. dry with materialthe crude product was dried under pump vacuum overnight

Sources & evidence

ORD record
ord-8818e11b97744c8290ea93cde9f8ba1f
Source dataset
uspto-grants-2007_07
Patent number
US07238699B2

Reaction notes

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