Phosphorus oxybromide → HCID 68896885, compound

HRID 1765383Notes

Reaction equation

HRID 1765383 reaction equation
[CH3:1][C:2]([S:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[NH:23][C:22](=O)[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:25])=[CH:10][CH:9]=1)(=[O:7])=[O:6])([CH3:4])[CH3:3].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:5]([C:2]([CH3:4])([CH3:3])[CH3:1])(=[O:7])=[O:6])=[CH:9][CH:10]=2)[N:23]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 68895530HCID 68895530, compound

Product 1

HCID 68896885HCID 68896885, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[4-(2-Methyl-propane-2-sulfonyl)-phenyl]-2,3-dihydro-phthalazine-1,4-dione (0.20 g, 0.56 mmol) and phosphorus oxybromide (0.48 g, 1.7 mmol) were stirred at 150° C. for 1 h. 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 preparative HPLC yielded the desired compound (0.06 g, 18%). 1H-NMR: (400 MHz, D6-DMSO) 8.41 (1H, d), 8.07 (1H, d), 8.03–8.10 (4H, m), 7.80 (2H, d), 1.30 (9H, s); MS (API+)=423.0 (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 preparative HPLC

Sources & evidence

ORD record
ord-d99f659cd0d64af4be72de0ee7338807
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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