Carbon Disulfide → 5-(trifluoromethyl)-1,3-benzothiazole-2-thiol

HRID 30889

Reaktionsgleichung

Reaktionsgleichung von HRID 30889
[H-].[Na+].C(OCCOCCO)C.Cl[C:13]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:14]=1[NH2:15].[C:24](=[S:26])=[S:25]>>[SH:26][C:24]1[S:25][C:13]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:14]=2[N:15]=1

Komponenten

5

Edukt 4

HCID 6348Carbon DisulfideHCID 8146Diethylene Glycol Monoethyl EtherHCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-HCID 24758Sodium hydride

Produkt 1

HCID 1784190875-(trifluoromethyl)-1,3-benzothiazole-2-thiolAusbeute 44,1 %

Versuchsvorschrift

To a mixture of sodium hydride (0.98 g, 40.91 mmol) and diethylene glycol monoethyl ether (25 mL) was added 2-chloro-5-(trifluoromethyl)aniline (5.00 g, 25.57 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at rt for 30 minutes, and then carbon disulfide (3.89 g, 51.13 mmol) was added. The reaction mixture was then heated at 140° C. for 6 hours. After cooling the solution to rt, the product was precipitated by addition of conc. HCl, collected by filtration, and recrystallized from isopropyl ether to afford 2-mercapto-5-(trifluoromethyl)benzothiazole (2.65 g, 44%). 1H NMR (400 MHz, DMSO-d6) δ 7.49 (s, 1H), 7.61 (d, 1H), 7.94 (d, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was then heated at 140° C. for 6 hours
  2. temperatureAfter cooling the solution to rt
  3. customthe product was precipitated by addition of conc. HCl
  4. filtrationcollected by filtration
  5. customrecrystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e73a0ffbefab444fb1cbfa75f1fe351c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423156B2

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