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

HRID 900879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 900879
[OH:1][CH2:2][C:3]([NH:6][S:7]([C:10]1[S:14][C:13]([NH:15]C(=O)C)=[N:12][CH:11]=1)(=[O:9])=[O:8])([CH3:5])[CH3:4]>Cl>[OH:1][CH2:2][C:3]([NH:6][S:7]([C:10]1[S:14][C:13]([NH2:15])=[N:12][CH:11]=1)(=[O:9])=[O:8])([CH3:5])[CH3:4]

Komponenten

3

Edukt 1

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

Produkt 1

HCID 866071052-Amino-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A stirred suspension of 2-acetamido-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (0.68 g, 2.32 mmol) in 6N hydrochloric acid (20 ml) was heated for 2 h at 80° C., evaporated., and saturated NaHCO3 solution (30 ml) was added. The mixture was extracted with ethyl acetate (3×50 ml), the combined organic layers washed with brine (30 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1) to yield the title compound (0.42 g, 72%) as a colorless oil. MS (ISP) 250.0 [(M−H)−].

Aufarbeitung

  1. customevaporated
  2. addition, and saturated NaHCO3 solution (30 ml) was added
  3. extractionThe mixture was extracted with ethyl acetate (3×50 ml)
  4. washthe combined organic layers washed with brine (30 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was further purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1)

Quellen und Nachweise

ORD-Eintrag
ord-af4fa95004fc41a0b2dbe25f2a7b1d7a
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361659B2

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