Benzoyl chloride → HCID 58979964, compound

HRID 1180679Notes

Reaction equation

[NH:1]1[C:5]([C:6]2[CH:19]=[CH:18][C:17]3[C:8](=[C:9]4[C:14](=[CH:15][CH:16]=3)[CH:13]=[CH:12][C:11]([C:20]3NN=[N:22][N:21]=3)=[N:10]4)[N:7]=2)=NN=[N:2]1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>N1C=CC=CC=1>[C:26]1([C:25]2[O:32][C:5]([C:6]3[CH:19]=[CH:18][C:17]4[C:8](=[C:9]5[C:14](=[CH:15][CH:16]=4)[CH:13]=[CH:12][C:11]([C:20]4[O:32][C:25]([C:26]6[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=6)=[N:22][N:21]=4)=[N:10]5)[N:7]=3)=[N:1][N:2]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Under nitrogen atmosphere, a mixture of 13 g (0.045 mol) 2,9-bis-(1H-tetrazol-5-yl)-[1,10]phenanthroline and 390 ml pyridine was added to a 250 ml three-necked flask. The mixture was then heated to 50° C., and 24.6 g (0.17 mol) benzoyl chloride was then added drop by drop. After the adding, the mixture solution was heated to reflux (110° C.) and stirred overnight. After completion of reaction, the reaction mixture was cooled to room temperature, filtered. Finally, solids were separated, washed by 100 ml methanol, filtered and purified by column chromatography to obtain white products 2,9-bis-(5-phenyl-[1,3,4]oxadiazol-2-yl)-[1,10]phenanthroline 4 g (0.008 mol, yield 17%). MS(m/z, FAB+), 468, 467, 307, 154, 105.

Workup

additionwas added to a 250 ml three-necked flask
temperatureAfter the adding, the mixture solution was heated
temperatureto reflux (110° C.)
customAfter completion of reaction
temperaturethe reaction mixture was cooled to room temperature
filtrationfiltered
customFinally, solids were separated
washwashed by 100 ml methanol
filtrationfiltered
custompurified by column chromatography

Sources & evidence

ORD record: ord-d2ee758ad1fb43bb903c3bdc81b85cd0
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282586B1

Reaction notes

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