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Dimethylformamide → HCID 178488015, Verbindung

HRID 1523358
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1523358
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:8](=S)[NH2:9])(C)C.O.[NH2:19]N.C[N:22]([CH:24]=O)C>C(O)=O>[CH3:1][O:4][C:5]1[CH:6]=[C:7]([C:8]2[N:22]=[CH:24][NH:19][N:9]=2)[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)HCID 86730375HCID 86730375, Verbindung

Produkt 1

HCID 178488015HCID 178488015, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

3-Isopropoxy-5-(trifluoromethyl)benzothioamide (646 g; 2.74 moles) was combined with hydrazine hydrate (140 g; 4.4 moles) and DMF (3200 mL; 5V). The mixture was stirred for 30 minutes and cooled to 10° C. To this reaction mixture was added formic acid (3200 mL) dropwise. Reaction mixture was heated to 90 to 100° C. and maintained for 12 hrs. After reaction completion by HPLC, reaction mass was cooled to 25 to 30° C. and quenched with ice-cold water. The mixture was extracted in MTBE. The organic layer was washed with brine followed by aqueous sodium bicarbonate, and concentrated under vacuum. The residue was chased off using hexane, the resulting residue was slurried at 10° C. for 1 hour. The solid obtained was filtered and dried for 12 hours at 25 to 30° C. to yield 550 g (2.26 moles: 82%) of the product 3-(3-methoxy-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazole. HPLC purity—95.24% a/a.

Aufarbeitung

  1. customReaction mixture
  2. temperaturewas heated to 90 to 100° C.
  3. temperaturemaintained for 12 hrs
  4. customAfter reaction completion
  5. customby HPLC, reaction mass
  6. temperaturewas cooled to 25 to 30° C.
  7. customquenched with ice-cold water
  8. extractionThe mixture was extracted in MTBE
  9. washThe organic layer was washed with brine
  10. concentrationconcentrated under vacuum
  11. waitthe resulting residue was slurried at 10° C. for 1 hour
  12. customThe solid obtained
  13. filtrationwas filtered
  14. customdried for 12 hours at 25 to 30° C.

Quellen und Nachweise

ORD-Eintrag
ord-fd9d462294fb43079283283263d286cc
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09079865B2

Notizen zur Reaktion

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