Phosphorus oxybromide → HCID 21106556, compound

HRID 1783698Notes

Reaction equation

HRID 1783698 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 RT. Extraction with DCM, 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:DCM (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 DCM
  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:DCM (2:1 to 0:1)

Sources & evidence

ORD record
ord-1e4b347d862345669bba467f15ee28c6
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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