Phosphorus oxychloride → HCID 20780222, compound

HRID 1349424Notes

Reaction equation

HRID 1349424 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-4b72c9d194f643e5a5e041014f34500e
Source dataset
uspto-grants-2007_05
Patent number
US07211669B2

Reaction notes

Loading…