Water → 5-Chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 900863

Reaktionsgleichung

Reaktionsgleichung von HRID 900863
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[Cl:7][C:8]1[S:12][C:11]([S:13](Cl)(=[O:15])=[O:14])=[CH:10][C:9]=1[N+:17]([O-:19])=[O:18].C(N(CC)CC)C.O>O1CCOCC1>[OH:4][CH2:3][C:2]([NH:1][S:13]([C:11]1[S:12][C:8]([Cl:7])=[C:9]([N+:17]([O-:19])=[O:18])[CH:10]=1)(=[O:15])=[O:14])([CH3:6])[CH3:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 27357835-Chloro-4-nitrothiophene-2-sulfonyl chloride

Produkt 1

HCID 672187905-Chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amideAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-amino-2-methyl-1-propanol (0.75 g, 8.39 mmol) in dioxane (21 ml) was added at room temperature 5-chloro-4-nitrothiophene-2-sulfonyl chloride (2.0 g, 7.63 mmol) and triethylamine (1.17 ml, 8.39 mmol). The light yellow suspension was stirred at room temperature for 17 h, poured into water (100 ml) and extracted with dichloromethane (3×75 ml). The combined organic layers were washed with water (100 ml) and brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1) and subsequent crystallization from ethyl acetate/hexane to yield 5-chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (0.73 g, 30%) as a light brown solid. MS (ISP) 313.1 [(M−H)−], mp 136° C.

Aufarbeitung

  1. extractionextracted with dichloromethane (3×75 ml)
  2. washThe combined organic layers were washed with water (100 ml) and brine (70 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1) and subsequent crystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-8b31cd04e9304f60aec365b95f3f653a
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361659B2

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