4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehyde → 1-(2-fluoro-6-propan-2-ylphenyl)-3-[(E)-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylideneamino]thiourea

HRID 1475612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1475612
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]([CH3:34])[CH3:33])[C:27]=1[NH:35][C:36]([NH:38][NH2:39])=[S:37]>CO>[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]([CH3:33])[CH3:34])[C:27]=1[NH:35][C:36]([NH:38]/[N:39]=[CH:19]/[C:18]1[CH:21]=[CH:22][C:15]([C:12]2[N:13]=[CH:14][N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:24])([F:23])[F:1])=[CH:5][CH:6]=3)[N:11]=2)=[CH:16][CH:17]=1)=[S:37]

Komponenten

4

Edukt 2

HCID 578244624-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehydeHCID 86691469N-(2-fluoro-6-isopropylphenyl)hydrazinecarbothioamide

Produkt 1

HCID 897237331-(2-fluoro-6-propan-2-ylphenyl)-3-[(E)-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylideneamino]thioureaAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehyde (0.760 g, 2.28 mmol) in methanol (22.8 mL) in a 100 mL round-bottomed flask equipped with a magnetic stir bar and reflux condenser was added N-(2-fluoro-6-isopropylphenyl)hydrazinecarbothioamide (0.518 g, 2.28 mmol), and the reaction was heated to 65° C. and stirred for 6 hours. The temperature was lowered to 50° C. and the reaction was stirred overnight. The reaction was cooled to room temperature and the resulting solid was filtered, washed with methanol, and dried under vacuum (25 in Hg) at 55° C. to give the title compound (0.907 g, 1.67 mmol, 73% yield) as a white solid: mp 210-212° C.; 1H NMR (400 MHz, CDCl3) δ 9.54 (s, 1H), 8.60 (s, 1H), 8.56 (s, 1H), 8.30-8.22 (m, 2H), 7.92 (s, 1H), 7.86-7.76 (m, 4H), 7.44-7.38 (m, 2H), 7.35 (dd, J=8.1, 5.6 Hz, 1H), 7.18 (d, J=7.9 Hz, 1H), 7.04 (ddd, J=9.4, 8.2, 1.3 Hz, 1H), 3.22 (p, J=6.9 Hz, 1H), 1.29 (d, J=6.9 Hz, 6H); ESIMS m/z 544 ([M+H]+).

Aufarbeitung

  1. temperaturereflux condenser
  2. customwas lowered to 50° C.
  3. stirringthe reaction was stirred overnight
  4. temperatureThe reaction was cooled to room temperature
  5. filtrationthe resulting solid was filtered
  6. washwashed with methanol
  7. customdried under vacuum (25 in Hg) at 55° C.

Quellen und Nachweise

ORD-Eintrag
ord-b4dc4878c74d4c7e80babfb93db2ac96
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018388B2

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