Reaction #452470

Reaction equation

diethyl ether

3-(imidazol-1-yl)propyl isothiocyanate

THF

THF

hydrogen bromide

→

title compound

Yield 75.0%

1-(3-(N-(4-Bromobenzyl)-N-(pyridin-2-yl)amino)propyl)-3-(3-(imidazol-1-yl)propyl)thiourea dihydrobromide

Yield 75.0%

Solvents

methanol

Conditions

Workup

1. 1
   Filtrationthe solid was filtered
2. 2
   OtherEvaporation of the filtrate under reduced pressure
3. 3
   Othergave a yellow oil which
4. 4
   Otherafforded a cloudy solution which
5. 5
   Otherproduced a light tan solid
6. 6
   FiltrationThe solid was filtered
7. 7
   Otherdried

Procedure

A solution of N-1-(4-bromobenzyl)-1-(pyrid-2-yl)propane-1,3-diamine (616 mg, 1.92 mmol) in THF (15 mL) was treated dropwise with 3-(imidazol-1-yl)propyl isothiocyanate (323 mg, 1.92 mmol) in THF (10 mL) under a nitrogen atmosphere. After stirring overnight at room temperature, the solid was filtered. Evaporation of the filtrate under reduced pressure gave a yellow oil which was dissolved in methanol and acidified with methanolic hydrogen bromide. Addition of diethyl ether afforded a cloudy solution which produced a light tan solid upon standing in the refrigerator. The solid was filtered and dried to yield 0.94 g (75%) of the title compound. Recrystallization from absolute ethanol-diethyl ether afforded an analytical sample.

Source