Iodine chloride → HCID 54711957, compound

HRID 2109830Notes

Reaction equation

HRID 2109830 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]3[C:13](=[O:19])[CH:14]=[C:15]([OH:18])[C:16]([OH:17])=[C:9]3[C:8]2=[O:20])=[CH:4][CH:3]=1.[I:23]Cl>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]3[C:13](=[O:19])[C:14]([I:23])=[C:15]([OH:18])[C:16]([OH:17])=[C:9]3[C:8]2=[O:20])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 54723326HCID 54723326, compound

Product 1

HCID 54711957HCID 54711957, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-(4-fluorobenzyl)-8,9-dihydroxy-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione (5 g, 16.4 mmol) in methylene chloride (300 mL) at room temperature, a solution of iodine monochloride (2.8 g, 17.2 mmol) in methylene chloride (50 mL) was added. The suspension was stirred at room temperature overnight and concentrated under vacuum. The residue was dissolved in ethyl acetate and washed subsequently with an aqueous solution of sodium metabisulfite and brine. The organic extract was dried over anhydrous magnesium sulfate, filtered, concentrated. The residual solid was stirred in diethyl ether overnight, and collected by filtration.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed subsequently with an aqueous solution of sodium metabisulfite and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. stirringThe residual solid was stirred in diethyl ether overnight
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-23e6e21620ca4a6a8e319502fdc9b6ef
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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