Ammonia tetrahydrofuran → 3-[5-(2-Fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzamide
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]=1Participants
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
- temperaturecooled to −78′C
- 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-a5ebea54f9154e73a8634269d65c328d
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710031B2
Reaction notes
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