Ethanol → 3-Ethoxy-5-[4-(trifluoromethyl)phenyl]-4H-1,2,4-triazole

HRID 650047Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([NH2:14])=[N:11][N:10]=2)=[CH:5][CH:4]=1.[OH-].[K+].[CH2:19](O)[CH3:20].[K+].[Br-]>C(O)(=O)C>[CH2:19]([O:13][C:12]1[NH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:16])([F:15])[F:1])=[CH:4][CH:5]=2)=[N:10][N:11]=1)[CH3:20]

Participants

Conditions

Temperature: 24 °C

Procedure

5-[4-(Trifluoromethyl)phenyl]1,3,4-oxadiazol-2-amine (10 g, 44 mmol) and potassium hydroxide (7.4 g, 0.132 mol) dissoved in abs. ethanol (300 ml) were heated at reflux for 3 h. After being cooled to 24° C., the solution was neutralized with acetic acid and concentrated by rotary evaporation. The residue was taken up in ethyl acetate and washed with water and brine. Recrystallization from acetonitrile/ether (2:1) gave 9 g (82%); mp 151-152° C.; IR(KBr, υ=cm−1) 2996, 1534, 1460, 1330, 1162, 1130, 1070; 1H NMR (300 MHz, DMSO-d6) δ 1.35 (3H, t, J=7.1 Hz), 4.38 (2H, q, J=7.0 Hz), 7.82 (2H, d, J=8.3 Hz), 8.10 (2H, d, J=8.1 Hz), 13.64 (1H, br. s); MS(DCl)m/z: 258 (MH+); Anal. calcd. for C11H10F3N3O: C, 51,37; H, 3.92; N, 16.34. Found: C, 51.40; H, 3.74; N, 16.28.

Workup

temperatureat reflux for 3 h
concentrationconcentrated by rotary evaporation
washwashed with water and brine
customRecrystallization from acetonitrile/ether (2:1)
customgave 9 g (82%)

Sources & evidence

ORD record: ord-907f3be1594a40b5a7c6f4536f6b09e0
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271249B1

Reaction notes

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