Phosphorus oxychloride → HCID 58058403, compound
Reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2-bromo-N-(2-(phenylamino)phenyl)benzamide (10.7 g, 29 mmol) in anhydrous 1,4-dioxane (˜100 mL), was added POCl3 (6.92 g, 45 mmol) slowly. The whole was heated to about 100° C. under argon overnight. After cooling the mixture to room temperature, the mixture was poured into ice (˜150 g), and then neutralized with NaHCO3. After filtration, the solid was collected then dissolved in dichloromethane (˜250 mL), which was washed with water (˜250 mL). The aqueous solution was extracted with dichloromethane (˜100 mL×2). The organic phase was combined and dried over Na2SO4, concentrated, and recrystallized in dichloromethane/hexanes to give a light grey solid (6.68 g, 66% yield).
Workup
- temperatureAfter cooling the mixture to room temperature
- filtrationAfter filtration
- customthe solid was collected
- dissolutionthen dissolved in dichloromethane (˜250 mL)
- washwhich was washed with water (˜250 mL)
- extractionThe aqueous solution was extracted with dichloromethane (˜100 mL×2)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customrecrystallized in dichloromethane/hexanes
Sources & evidence
- ORD record
- ord-1c727a15db3e407ba687896989370c8b
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08808879B2
Reaction notes
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