Benzoyl isothiocyanate → 1-[2-(1H-Benzimidazol-2-yl)ethyl]thiourea

{2-(1H-Benzimidazol-2-yl)ethylamine was made as the dihydrochloride salt according to a procedure described by Nicolaou et al. Bioorg. Med. Chem., 1998, 6, 1185-1208 and pretreated with DIPEA (2.07 mL, 11.86 mmol) for 5 minutes.} To a suspension of 2-(1H-benzimidazol-2-yl)ethylamine (1.39 g, 5.93 mmol) in dichloromethane (20 mL) was added benzoyl isothiocyanate (0.88 mL, 6.52 mmol). After 1 h, the reaction mixture was concentrated in vacuo. Ammonia in methanol (7N, 30 mL) was then added and the reaction stirred another 4 h. The excess ammonia and methanol were removed in vacuo and dichloromethane (15 mL) was added. The solid was removed by filtration and the filtrate concentrated in vacuo and purified by flash chromatography (methanol/dichloromethane, 5% then 10%) to give the title compound as a solid (1.12 g, 86% yield).

1. concentrationthe reaction mixture was concentrated in vacuo
2. additionAmmonia in methanol (7N, 30 mL) was then added
3. customThe excess ammonia and methanol were removed in vacuo and dichloromethane (15 mL)
4. additionwas added
5. customThe solid was removed by filtration
6. concentrationthe filtrate concentrated in vacuo
7. custompurified by flash chromatography (methanol/dichloromethane, 5%

ORD record

ord-a74f91f5d9b844d1a4977d13d6fdf909

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026244B2