Reaktion #429155

Reaktionsgleichung

sodium hydroxide

2-imino-4-thiobiuret

3-chloropropionitrile

1,3-dichloroacetone

thiourea

→

N-[4-(cyanoethylthiomethyl)-2-thiazolyl]guanidine

Ausbeute 61.1%

Lösungsmittel

water

isopropyl alcohol

water

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 500 mL round bottom flask equipped with an overhead stirrer and under an inert atmosphere
2. 2
   TemperaturThe reaction mixture was then heated to 40° C.
3. 3
   TemperaturThe mixture was heated to and
4. 4
   workup.WAITheld at 52° C. for one hour
5. 5
   SonstigeAcetone was then removed by vacuum distillation
6. 6
   TemperaturThe reaction mixture was cooled below 10° C.
7. 7
   Temperaturmaintaining the reaction temperature below 10° C
8. 8
   workup.WAITThe reaction mixture was for 2 hours
9. 9
   Filtrationfiltered
10. 10
    Waschenwashed

Vorschrift

Into a 500 mL round bottom flask equipped with an overhead stirrer and under an inert atmosphere was added 25 g of 1,3-dichloroacetone (0.197 mol) and 75 g of acetone. The reaction mixture was cooled to 10° C. and 23.2 g 2-imino-4-thiobiuret (0.197 mol) was added. The reaction mixture was stirred for one hour at 10 C. The reaction mixture was then heated to 40° C. and 15 g of thiourea (0.197 mol) was added, followed by the addition of 100 g of water. The mixture was heated to and held at 52° C. for one hour. Acetone was then removed by vacuum distillation. To the reaction mixture was added 100 g of water, 17 g of 3-chloropropionitrile (0.190 mol) and 40 g of isopropyl alcohol. The reaction mixture was cooled below 10° C. and 25 g of an aqueous solution of sodium hydroxide (80 g water) was added dropwise maintaining the reaction temperature below 10° C. The reaction mixture was for 2 hours, filtered and washed to produce 28 g of N-[4-(cyanoethylthiomethyl)-2-thiazolyl]guanidine product.

Quelle