Ammonia → 1-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

HRID 1803107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803107
[NH3:1].[F:2][C:3]1[C:4]([N:17]=[C:18]=[S:19])=[CH:5][C:6]([O:15][CH3:16])=[C:7]([N:9]2[CH:13]=[N:12][C:11]([CH3:14])=[N:10]2)[CH:8]=1>>[F:2][C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[N:12][C:11]([CH3:14])=[N:10]2)[C:6]([O:15][CH3:16])=[CH:5][C:4]=1[NH:17][C:18]([NH2:1])=[S:19]

Komponenten

3

Edukt 2

HCID 222AmmoniaHCID 866498891-(5-fluoro-4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole

Produkt 1

HCID 866498901-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thioureaAusbeute 100,5 %

Versuchsvorschrift

Step B (4): Methanolic ammonia (1.0 M, 25 mL, 25 mmol) was added to a flask charged with 1-(5-fluoro-4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole (870 mg, 3.29 mmol) in a ice-water bath. After the addition was complete, the resulting slurry was stirred for 10 min and then allowed to warm to rt. After 24 h, the reaction mixture was concentrated in vacuo. The resulting solid was dried under high vacuum to afford 1-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (930 mg, 100% yield). LC-MS (M+H)+ 282.1. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.84 (s, 1 H) 7.88 (d, J=6.41 Hz, 1 H) 7.57 (d, J=10.99 Hz, 1 H) 3.86 (s, 3 H) 2.36 (s, 3 H).

Aufarbeitung

  1. additionAfter the addition
  2. waitAfter 24 h
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe resulting solid was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-722d3f53831c4ef1a257f73067a10e87
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349880B2

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