Triphosgene → HCID 21069694, compound

HRID 1371257Notes

Reaction equation

HRID 1371257 reaction equation
Cl[C:2](Cl)([O:4][C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[Br:13][C:14]1[CH:23]=[C:22]([Br:24])[C:21]([CH2:25]CO)=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[N:19]2>O1CCOCC1>[Br:13][C:14]1[CH:23]=[C:22]([Br:24])[C:21]([CH2:25][CH2:2][O:4][C:5]([O:6][CH3:7])=[O:11])=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[N:19]2

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 11186570HCID 11186570, compound

Product 1

HCID 21069694HCID 21069694, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Triphosgene, 740 mg (2.5 mmol) was dissolved in 5 mL of anhydrous dioxane and stirred at ambient temperature while 5,7-dibromo-8-(2-hydroxyethyl)quinoline was added in several portions. The mixture was stirred overnight and capped to protect from atmospheric moisture. The solvent and excess reagent were removed under a stream of dry argon. Residue was redissolved in 10 mL of methanol, stirring for 1 hr., and the solvent was removed. The residue was recrystallized from methanol/water. Melting point: 102.5104.5° C.

Workup

  1. additionwas added in several portions
  2. customcapped
  3. customThe solvent and excess reagent were removed under a stream of dry argon
  4. dissolutionResidue was redissolved in 10 mL of methanol
  5. stirringstirring for 1 hr
  6. custom, and the solvent was removed
  7. customThe residue was recrystallized from methanol/water
  8. custom5104.5° C.

Sources & evidence

ORD record
ord-d1ff12d08f424a3f913e1340e33c9403
Source dataset
uspto-grants-2007_01
Patent number
US07157408B2

Reaction notes

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