1,1'-Carbonyldiimidazole → 3-(3-(4-Methyl-3-nitrophenyl)-1,2,4-oxadiazol-5-yl)cyclobutanone

HRID 1497897Notes

Reaction equation

[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.O[N:22]=[C:23]([NH2:34])[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([N+:31]([O-:33])=[O:32])[CH:25]=1>CN1CCCC1=O.C(OCC)(=O)C.O>[CH3:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]2[N:22]=[C:6]([CH:4]3[CH2:3][C:2](=[O:1])[CH2:5]3)[O:8][N:34]=2)=[CH:25][C:26]=1[N+:31]([O-:33])=[O:32]

Participants

Conditions

Temperature: 130 °C

Procedure

To a stirring solution of 3-oxocyclobutanecarboxylic acid (595 mg, 5.12 mmol) in 1-methyl-2-pyrrolidinone (6 mL) was added 1,1′-carbonyldiimidazole (831 mg, 5.12 mmol). The reaction was stirred for 5 minutes. Then, N′-hydroxy-4-methyl-3-nitrobenzimidamide (27) (500 mg, 2.56 mmol) was added and the reaction was stirred for 15 minutes. Next, the reaction was heated in the microwave at 130° C. for 10 minutes. The crude product was taken in ethyl acetate and water. The organic was washed with 2× water/brine mixture and dried over anhydrous sodium sulfate. The solvent was concentrated and the crude product was purified by silica chromatography to afford 3-(3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazol-5-yl)cyclobutanone (122). MS m/z 274.07 (M+1)+.

Workup

stirringthe reaction was stirred for 15 minutes
washThe organic was washed with 2× water/brine mixture
dry with materialdried over anhydrous sodium sulfate
concentrationThe solvent was concentrated
customthe crude product was purified by silica chromatography

Sources & evidence

ORD record: ord-aac2f65562774674a97104b928ced82e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199981B2

Reaction notes

Loading…