Diethanolamine → 5-Chloro-4-nitro-thiophene-2-sulfonic acid bis-(2-hydroxy-ethyl)-amide

To a stirred solution of diethanolamine (1.16 g, 11 mmol) in water (4 ml) was added at room temperature magnesium oxide (2.22 g, 55 mmol) and THF (16 ml). The suspension was stirred at room temperature for 30 min and a solution of 5-chloro-4-nitrothiophene-2-sulfonyl chloride (3.46 g, 13.2 mmol) in THF (4 ml) was added. The light yellow suspension was stirred at room temperature for 1 h and, after filtration on Dicalit, evaporated. Water (60 ml) was added and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate) to yield 5-chloro-4-nitro-thiophene-2-sulfonic acid bis-(2-hydroxy-ethyl)-amide (0.48 g, 13%) as a yellow solid. MS (ISP) 331.2 [(M+H)+], mp 113° C.

1. stirringThe light yellow suspension was stirred at room temperature for 1 h
2. filtrationafter filtration on Dicalit
3. customevaporated
4. additionWater (60 ml) was added
5. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
6. washThe combined organic layers were washed with brine (70 ml)
7. dry with materialdried (MgSO4)
8. customevaporated
9. customThe crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate)

ORD-Eintrag

ord-2000cf77dc2e495683fce9bfce4e467f

Quelldatensatz

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07361659B2