Reaktion #74914

Reaktionsgleichung

1-diphenylmethyl-2-methylthiopseudourea hydroiodide

1,4-diaminobutane

methyl mercaptan

→

2-diphenylmethylamino-4,5,6,7-tetrahydro-1H-1,3-diazepine hydroiodide

Lösungsmittel

o-dichlorobenzene

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturunder reflux overnight (about 19 hours)
3. 3
   TemperaturWhile the mixture was still warm
4. 4
   Sonstigethe solvent was decanted from the oily layer
5. 5
   workup.ADDITIONdiluted with about 1.5 liters of ether
6. 6
   Temperaturcooled
7. 7
   Sonstigeto form
8. 8
   Sonstigestored at -23° C., whereupon it
9. 9
   Sonstigethe gum was separated from the mother liquor by decantation
10. 10
    workup.DISSOLUTIONredissolved in fresh isopropanol whereupon a dark solid
11. 11
    Sonstigeseparated
12. 12
    SonstigeThe light colored crystals from the ether and the dark solid from the isopropanol were separately recrystallized
13. 13
    Sonstigeto obtain white crystals
14. 14
    SonstigeThe white crystals separately obtained
15. 15
    Sonstigerecrystallized from the same solvent pair

Vorschrift

A suspension of 38.43 grams (0.1 mole) of 1-diphenylmethyl-2-methylthiopseudourea hydroiodide and 8.82 grams (0.1 mole) of 1,4-diaminobutane in 500 milliliters of o-dichlorobenzene was stirred and heated under reflux overnight (about 19 hours). During the heating a reaction took place with the evolution of a basic gas and methyl mercaptan and the formation of a dark oily layer. While the mixture was still warm, the solvent was decanted from the oily layer, diluted with about 1.5 liters of ether and cooled. Scratching of the ether solution caused light colored crystals to form. The dark oily residue was taken up in about 75 milliliters of isopropanol and stored at -23° C., whereupon it came a semisolid gum; the gum was separated from the mother liquor by decantation and redissolved in fresh isopropanol whereupon a dark solid separated. The light colored crystals from the ether and the dark solid from the isopropanol were separately recrystallized using activated carbon and methanol-isopropanol mixture as solvent to obtain white crystals. The white crystals separately obtained were combined and recrystallized from the same solvent pair to obtain a purified 2-diphenylmethylamino-4,5,6,7-tetrahydro-1H-1,3-diazepine hydroiodide product m.p. 215°-217.5° C.

Quelle