Hydrochloric Acid → N-(4-bromo-2-fluorophenyl)-4-methyl-1,3-benzothiazol-2-amine

HRID 907723

Reaktionsgleichung

Reaktionsgleichung von HRID 907723
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=2[N:6]=1.[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([F:20])[CH:14]=1.Cl>CCCCO>[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[S:3][C:4]3[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=3[N:6]=2)=[C:15]([F:20])[CH:14]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 1230504-Bromo-2-fluoroanilineHCID 20498602-Chloro-4-methylbenzothiazole

Produkt 1

HCID 23549342N-(4-bromo-2-fluorophenyl)-4-methyl-1,3-benzothiazol-2-amineAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 2-chloro-4-methyl-1,3-benzothiazole (0.25 g, 1.36 mmol) in n-BuOH (8 mL) was added 4-bromo-2-fluoroaniline (0.52 g, 2.72 mmol) and HCl (4.0 M in dioxane, 0.5 mL). The reaction was heated at 90° C. overnight. Solvent was removed by rotary evaporation and 1 N aqueous HCl was added. The aqueous layer was separated and extracted with EtOAc. The combined organic phases were washed with 1 N aqueous HCl and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was brought up in MeOH and the precipitate was collected by filtration, washed with MeOH, and dried in a vacuum oven to give N-(4-bromo-2-fluorophenyl)-4-methyl-1,3-benzothiazol-2-amine (0.41 g, 89%). 1H NMR (400 MHz, DMSO-d6) δ 2.62 (s, 3H), 7.07 (t, 1H), 7.15 (d, 1H), 7.36 (m, 2H), 7.51 (d, 1H), 8.72 (t, 1H).

Aufarbeitung

  1. customSolvent was removed by rotary evaporation and 1 N aqueous HCl
  2. additionwas added
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc
  5. washThe combined organic phases were washed with 1 N aqueous HCl and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with MeOH
  11. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-5f52998183bf4d549171ac40f0245f40
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013166B2

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