Triethylamine → 2-Acetamido-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 900878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 900878
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[C:7]([NH:10][C:11]1[S:12][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:14][N:15]=1)(=[O:9])[CH3:8].C(N(CC)CC)C>O1CCOCC1>[OH:4][CH2:3][C:2]([NH:1][S:16]([C:13]1[S:12][C:11]([NH:10][C:7](=[O:9])[CH3:8])=[N:15][CH:14]=1)(=[O:17])=[O:18])([CH3:6])[CH3:5]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 3502612-Acetamido-1,3-thiazole-5-sulfonyl chloride

Produkt 1

HCID 866071042-Acetamido-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amideAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-amino-2-methyl-1-propanol (1.11 g, 12.5 mmol) in dioxane (20 ml) was added at 0° C. (ice water bath) 2-acetamido-thiazole-5-sulfonyl chloride [CAS No. 69812-30-2; commercially available] (1.0 g, 4.15 mmol) and triethylamine (0.64 ml, 4.57 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate) to yield 2-acetamido-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (0.72 g, 59%) as a white solid. MS (ISP) 292.1 [(M−H)−]; mp 206° C.

Aufarbeitung

  1. customevaporated
  2. customThe crude product was further purified by column chromatography on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-53f020358d444c26824190e9707b4452
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361659B2

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