ethyl (2Z)-2-amino-2-[2-(2,5-difluorophenyl)acetyl]oxyiminoacetate → Ethyl 5-(2,5-difluorobenzyl)-1,2,4-oxadiazole-3-carboxylate

HRID 58574Notes

Reaction equation

[NH2:1]/[C:2](=[N:8]\[O:9][C:10](=O)[CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[F:19])/[C:3]([O:5][CH2:6][CH3:7])=[O:4]>N1C=CC=CC=1>[F:19][C:13]1[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=1[CH2:11][C:10]1[O:9][N:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:1]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(Z)-ethyl 2-amino-2-(2-(2,5-difluorophenyl)acetoxyimino)acetate (0.455 g; 1.59 mmol) was dissolved in pyridine (10 mL). The solution was heated at 120° C. for 2 h and was evaporated to dryness. The residue was purified by flash chromatography on silica gel (eluent: 0 to 20% of ethyl acetate in dichloromethane) to give 0.301 g (71%) of ethyl 5-(2,5-difluorobenzyl)-1,2,4-oxadiazole-3-carboxylate as a white solid.

Workup

customwas evaporated to dryness
customThe residue was purified by flash chromatography on silica gel (eluent: 0 to 20% of ethyl acetate in dichloromethane)

Sources & evidence

ORD record: ord-dfb1231a95d04821a5d03bafd75b6bab
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434722B2

Reaction notes

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