Phosphorus oxybromide → HCID 21106556, compound

HRID 1765385Notes

Reaction equation

HRID 1765385 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[NH:23][C:22](=O)[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]3=[O:25])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)([Br:28])=O>O>[Br:28][C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:25])[N:14]([C:11]2[CH:12]=[CH:13][C:8]([S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:9][CH:10]=2)[N:23]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 21106520HCID 21106520, compound

Product 1

HCID 21106556HCID 21106556, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(4-Phenylsulfanyl-phenyl)-2,3-dihydro-phthalazine-1,4-dione (0.10 g, 0.29 mmol) and phosphorus oxybromide (0.33 g, 12 mmol) were stirred at 150° C. for 40 min. H2O (50 ml) was added after cooling to room temperature. Extraction with dichloromethane, drying of the combined organic phases over Na2SO4, evaporation of the solvent and purification of the raw product by chromatography over silica gel with heptane:dichloromethane (2:1 to 0:1) gave the desired compound (0.10 g, 86%). 1H-NMR: (400 MHz, D6-DMSO) 8.36 (1H, d), 8.11 (1H, d), 8.00 (2H, m), 7.65 (2H, d), 7.44 (7H, m); MS (ESI+)=411.2 (M+H)+.

Workup

  1. extractionExtraction with dichloromethane
  2. dry with materialdrying of the combined organic phases over Na2SO4, evaporation of the solvent and purification of the raw product by chromatography over silica gel with heptane:dichloromethane (2:1 to 0:1)

Sources & evidence

ORD record
ord-5aaeed235fb4478a882ab4a4eca2faa7
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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