Water → HCID 10047941, compound

HRID 362455Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([C:13]2[N:14]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=3[O:26]C)[C:15](=[O:18])[NH:16][N:17]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl.N1C=CC=CC=1.O>C(OCC)(=O)C>[Cl:25][C:23]1[CH:22]=[CH:21][C:20]([OH:26])=[C:19]([N:14]2[C:13]([C:5]3[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:28])([F:1])[F:29])[CH:4]=3)=[N:17][NH:16][C:15]2=[O:18])[CH:24]=1

Participants

Conditions

Temperature: 225 °C

Procedure

5-[3,5-Bis(trifluoromethyl)phenyl]-4-(5-chloro-2-methoxy phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (1.6 g, 3.6 mmol) was admixed with pyridine hydrochloride (6.7 g, 58 mmol) and heated at 225° C. for 1 h. After being cooled, the solid was covered with ethyl acetate (25 ml) and water (15 ml) and subjected to ultrasonication (bath) for several minutes in order to break the solid free from the glass wall. The organic suspension was diluted with ethyl acetate (100 ml) washed with water (25 ml), saturated sodium carbonate solution (25 ml), and brine. Concentration gave a solid 1.46 g (95%) which was recrystallized from acetonitrile. mp 275°-278° C. IR(KBr, ν=cm-1) 3166,1681, 1314, 1275, 1180, 1140; 1H NMR (300 MHz, DMSO6) δ6.92 (1H, d, J=8.8 Hz), 7.38 (1H, dd, J=8.8 Hz, 2.6 Hz), 7.58 (1H, d, J=2 Hz), 7.91 (2H, s), 8.17 (1H, s), 10.45 (1H, s), 10.45 (1H, s), 12.44 (1H, s); MS(DCl)m/z: 424(MH+).

Workup

temperatureAfter being cooled
customsubjected to ultrasonication (bath) for several minutes in order
washwashed with water (25 ml), saturated sodium carbonate solution (25 ml), and brine
concentrationConcentration

Sources & evidence

ORD record: ord-51cae3601a244388a4d59d761dc37944
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869509

Reaction notes

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