Water → 1-(Ethylsulfanyl)-4-nitrobenzene

Temperature

60 °C

Ethanethiol (6.11 ml, 0.082 mol) was added slowly to a suspension of sodium hydride (3.3 g, 60% dispersion) in dry dimethylformamide (225 ml) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred for 15 min before the addition of 1-chloro-4-nitrobenzene (10 g, 0.063 mol) dissolved in dry dimethylformamide (25 ml). After addition, the resultant mixture was allowed to warm to 60° C. and was stirred for 24 hr. The mixture was then concentrated in vacuo to yield a yellow oil. Ice and water were added and a yellow solid was precipitated and filtered off. The solid was then dissolved in methanol (100 ml) and insoluble by-products were isolated by filtration. The filtrate was then concentrated in vacuo. The residue was dissolved in ethyl acetate (50 ml) and washed with water (2×50 ml). The organic layer was then dried (MgSO4) and concentrated in vacuo to afford 1-(ethylthio)-4-nitrobenzene as a yellow solid. δ(1H NMR, DMSO, ppm): 1.15 (3H, t), 3.05 (2H, q) 7.45 (2H, d), 8.10 (2H, d)

1. additionAfter addition
2. concentrationThe mixture was then concentrated in vacuo
3. customto yield a yellow oil
4. customa yellow solid was precipitated
5. filtrationfiltered off
6. dissolutionThe solid was then dissolved in methanol (100 ml)
7. custominsoluble by-products were isolated by filtration
8. concentrationThe filtrate was then concentrated in vacuo
9. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
10. washwashed with water (2×50 ml)
11. dry with materialThe organic layer was then dried (MgSO4)
12. concentrationconcentrated in vacuo

ORD record

ord-65f189320abe4e7eb467399cc36d1654

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06329366B1