Reaktion #463000

Reaktionsgleichung

chloromethyithiocyanate

sodium sulfide

4-Phenyl-3-chloro-1,2,5-thiadiazole

dimethylformamide

→

4-Phenyl-3-thiocyanato-methylthio-1,2,5-thiadiazole

Ausbeute 69.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThis mixture was stirred for ~14 hours
2. 2
   Extraktionextracted with 200 mL of methylene chloride
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with water (2×100 mL)
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe thus recovered crude material
8. 8
   Sonstigewas chromatographed on silica gel with a 10% EtoAc
9. 9
   Sonstige90% hexane mixture to yield 8.99 g (83 percent of theoretical) as an oil
10. 10
    SonstigeUpon crystallization
11. 11
    Sonstigea light yellow solid melting at 58°-60° C. was recovered in a yield of 69 percent of theoretical

Vorschrift

To a stirred solution of 3.81 grams(g)(0.05 mole) of sodium sulfide in 100 mL of dimethylformamide was added 8 g (0.041 mole) of 4-Phenyl-3-chloro-1,2,5-thiadiazole. The mixture was stirred 18 hours and to this mixture was added 6.68 g (1.5 molar equivalents) of chloromethyithiocyanate. This mixture was stirred for ~14 hours and then diluted with 100 mL of water and extracted with 200 mL of methylene chloride. The organic layer was separated and washed with water (2×100 mL), dried and concentrated under reduced pressure. The thus recovered crude material was chromatographed on silica gel with a 10% EtoAc:90% hexane mixture to yield 8.99 g (83 percent of theoretical) as an oil. Upon crystallization, a light yellow solid melting at 58°-60° C. was recovered in a yield of 69 percent of theoretical; 1H NMR (300 MHz, CDCl3)δ 4.77 (s, 2H), 7.49 (m, 3H), 7.82 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 38.28, 111.46, 127.97, 128.78, 130.06, 151.77, 157.93; MS (EI) m/e 265(M+), 207, 148, 116.

Quelle