Diethyl benzylphosphonate → HCID 131723929, compound

HRID 1370604Notes

Reaction equation

[CH2:1](P(=O)(OCC)OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([N:26]([C:34]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:41]([C:48]3[C:49]4[C:54]([C:55]([N:62]([C:71]5[CH:76]=[CH:75][CH:74]=[CH:73][C:72]=5[CH3:77])[C:63]5[CH:68]=[CH:67][C:66]([CH:69]=O)=[CH:65][CH:64]=5)=[C:56]5[C:61]=3[CH:60]=[CH:59][CH:58]=[CH:57]5)=[CH:53][CH:52]=[CH:51][CH:50]=4)=[C:40]3[C:35]=2[CH:36]=[CH:37][CH:38]=[CH:39]3)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])=[CH:22][CH:21]=1)=O>CS(C)=O>[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([N:26]([C:34]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:41]([C:48]3[C:49]4[C:54]([C:55]([N:62]([C:71]5[CH:76]=[CH:75][CH:74]=[CH:73][C:72]=5[CH3:77])[C:63]5[CH:68]=[CH:67][C:66]([CH:69]=[CH:1][C:2]6[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=6)=[CH:65][CH:64]=5)=[C:56]5[C:61]=3[CH:60]=[CH:59][CH:58]=[CH:57]5)=[CH:53][CH:52]=[CH:51][CH:50]=4)=[C:40]3[C:35]=2[CH:36]=[CH:37][CH:38]=[CH:39]3)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])=[CH:22][CH:21]=1)=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

10,10′-Bis(p-tolylphenylamino)-9,9′-bianthryl(19 g; yield 54%) was prepared as described in Preparation Example 3, except that 20 g of diphenylamine was replaced with 22 g of p-tolylphenylamine. Then, 7 g of 10,10′-bis(p-tolylphenylamino)-9,9′-bianthryl was dissolved in 50 mL of toluene, to which 3.7 g of phosphorus oxychloride was then added, and the mixture was stirred at room temperature. To the mixture was added dropwise 2.7 g of N-methylformanilide, and the mixture was stirred at 50° C. for 5 hours. After completion of the reaction, the mixture was slowly poured into 100 mL of cold water. The mixture was transferred into a separatory funnel and the toluene layer was washed several times until pH of the washing become neutral. The organic layer was dried over magnesium sulfate and evaporated to give 4.5 g (yield 60%) of 10,10′-bis(N-p-formylphenyl-N-tolylamino)-9,9′-bianthryl. To 50 mL of dimethylsulfoxide were added 2.9 g of diethyl benzylphosphonate and 0.6 g of sodium hydride. To the stirred mixture was added dropwise 4.5 g of 10,10′-bis(N-p-formylphenyl-N-tolylamino)-9,9′-bianthryl in 50 mL of dimethylsulfoxide, and the reaction mixture was stirred at 50° C. for 3 hours. After completion of the reaction, the solution was poured into 50 mL of ice-water. The mixture was neutralized with an acid and extracted with ethyl acetate. After evaporating the solvent under a reduced pressure, the residue was purified by column chromatography on silica gel eluting with chloroform, and the product was recrystallized from ethanol to give 3.8 g (yield 70%) of 10,10′-bis(N-p-styrylphenyl-N-tolylamino)-9,9′-bianthryl.

Workup

customAfter completion of the reaction
extractionextracted with ethyl acetate
customAfter evaporating the solvent under a reduced pressure
customthe residue was purified by column chromatography on silica gel eluting with chloroform
customthe product was recrystallized from ethanol

Sources & evidence

ORD record: ord-c2af1d37d33c4d17bff11f4a1b78a732
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06582837B1

Reaction notes

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