反応 #312293

反応方程式

1-diphenylmethyl-2-methylthiopseudourea hydroiodide

1,4-diaminobutane

methyl mercaptan

→

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

溶媒

o-dichlorobenzene

isopropanol

反応条件

後処理

1. 1
   温度heated
2. 2
   温度under reflux overnight (about 19 hours)
3. 3
   温度While the mixture was still warm
4. 4
   その他the solvent was decanted from the oily layer
5. 5
   workup.ADDITIONdiluted with about 1.5 liters of ether
6. 6
   温度cooled
7. 7
   その他to form
8. 8
   その他stored at -23° C., whereupon it
9. 9
   その他the gum was separated from the mother liquor by decantation
10. 10
    workup.DISSOLUTIONredissolved in fresh isopropanol whereupon a dark solid
11. 11
    その他separated
12. 12
    その他The light colored crystals from the ether and the dark solid from the isopropanol were separately recrystallized
13. 13
    その他to obtain white crystals
14. 14
    その他The white crystals separately obtained
15. 15
    その他recrystallized from the same solvent pair

実験手順

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.

出典