Diethyl Ether → ethyl [(1-benzyl-1H-benzimidazol-2-yl)sulfanyl]acetate

Temperatur

0 °C

To a stirred solution of ethyl 2-(1H-benzo[d]imidazol-2-ylthio)acetate 4a (11.2 g, 47.6 mmol, 1.0 eq.) in 10:1 diethyl ether:dimethylformamide (450 mL) at 0° C., was added 60% sodium hydride in mineral oil (2.09 g, 52.3 mmol, 1.1 eq.), and the reaction was stirred at 0° C. for 20 minutes. Benzyl bromide (9.78 g, 57.1 mmol, 1.2 eq.) was added at 0° C., and the reaction was stirred with warming to room temperature for 16 hours. The reaction mixture was quenched with methanol (100 mL) and concentrated in vacuo. The residue was taken into hot chloroform (400 mL) and filtered. The filtrate was washed with water (200 mL), 1M HCl (200 mL) and brine (200 mL). The organic layer was dried over magnesium sulfate and concentrated in vacuo. Purification by flash chromatography (10% EtOAc:90% petroleum ether) gave 4b as a pale-yellow solid (4.82 g, 30%).

1. stirringthe reaction was stirred
2. temperaturewith warming to room temperature for 16 hours
3. customThe reaction mixture was quenched with methanol (100 mL)
4. concentrationconcentrated in vacuo
5. filtrationfiltered
6. washThe filtrate was washed with water (200 mL), 1M HCl (200 mL) and brine (200 mL)
7. dry with materialThe organic layer was dried over magnesium sulfate
8. concentrationconcentrated in vacuo
9. customPurification by flash chromatography (10% EtOAc:90% petroleum ether)

ORD-Eintrag

ord-78ec53df199c44c4b210f4fb9b37d8e2

Quelldatensatz

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08278327B2