Water → HCID 4994359, compound

HRID 2080810Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]1([CH3:19])[CH:15]=[CH:14][C:13]([C:16](Cl)=[O:17])=[CH:12][CH:11]=1.O>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:16](=[O:17])[C:13]2[CH:14]=[CH:15][C:10]([CH3:19])=[CH:11][CH:12]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

Conditions

Temperature: 0 °C

Procedure

4-Aminobenzonitrile (1.10 g) was dissolved in chloroform (30 ml). After having been cooled to 0° C., the reaction solution was added with 4-dimethylaminopyridine (1.70 g) and p-toluic acid chloride (1.95 g). The reaction solution was warmed back to room temperature and stirred overnight. The reaction solution was added with distilled water and subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure. The resultant residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and then purified by recrystallization (hexane/ethanol), thereby obtaining the subject compound (1.26 g) as a white solid.

Workup

temperatureThe reaction solution was warmed back to room temperature
extractionsubjected to extraction with chloroform
washThe organic layer was washed with a saturated saline solution
dry with materialdried with anhydrous sodium sulfate
concentrationThe organic layer was concentrated under reduced pressure
customThe resultant residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
custompurified by recrystallization (hexane/ethanol)

Sources & evidence

ORD record: ord-b1744120a0ff4cb383641859d61cee5e
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932281B2

Reaction notes

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