Ammonia tetrahydrofuran → 3-[5-(2-Fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzamide

HRID 920884Notes

Reaction equation

[NH3:1].C1COCC1.[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22](Cl)=[O:23])[N:15]=1>O1CCCC1>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([NH2:1])=[O:23])[N:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Saturated NH3/THF solution (130 ml) cooled to 0° C. via cannula slowly over 10 min is then added to a suspension of 3-[5-(2-fluorophenyl)-[1,2,4]oxadiazol-3-yl]-benzoyl chloride (Compound A2, 8.0 g, 26.43 mmol) in anhydrous tetrahydrofuran (80 mL) cooled to −78° C. The mixture is stirred for 30 minutes, warmed to room temperature and stirred for 16 h. The solvent is concentrated in vacuo and the resulting white residue is washed several times with water. The wet solid is dried in a vacuum oven for two days to give 7.06 g (94%) of 3-[5-(2-fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzamide (Compound A3) as a white solid: mp 231-234° C.; 1H NMR (300 MHz, DMSO-d6) δ 6.10 (br d, J=9.7 Hz, 2H) 7.28-7.39 (m, 2H), 7.64 (t, J=7.8 Hz, 2H), 8.07 (d, J=7.8 Hz, 1H), 8.24 (t, J=7.5 Hz, 1H), 8.37 (d, J=7.5 Hz, 1H), 8.58 (t, J=1.8 Hz, 1H); MS m/z 284.12, calcd for C15H10FN3O2 (MH+) 284.

Workup

temperaturewarmed to room temperature
stirringstirred for 16 h
concentrationThe solvent is concentrated in vacuo
washthe resulting white residue is washed several times with water
customThe wet solid is dried in a vacuum oven for two days

Sources & evidence

ORD record: ord-c6f8d912c64a4fb4a245b73e2aca549a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273076B2

Reaction notes

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