Pyridine → 4-bromo-N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-5-chlorothiophene-2-sulfonamide

HRID 252240

Reaktionsgleichung

Reaktionsgleichung von HRID 252240
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[S:5][C:6]=1[Cl:7].N1C=CC=CC=1.[O-:18][C:19]#[N:20].[Na+].Br.[Br:23][C:24]1[S:28][C:27]([NH2:29])=[N:26][CH:25]=1>C(#N)C.C(O)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:20][C:19](=[O:18])[NH:29][C:27]2[S:28][C:24]([Br:23])=[CH:25][N:26]=2)(=[O:10])=[O:9])[S:5][C:6]=1[Cl:7]

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 517096Sodium CyanateHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 27972204-Bromo-5-chlorothiophene-2-sulfonyl chloride

Produkt 1

HCID 247523614-bromo-N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-5-chlorothiophene-2-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-Bromo-5-chloro-thiophene-2-sulfonyl chloride (0.44 g, 1.50 mmol) and pyridine (0.27 ml, 3.40 mmol) were added to a stirred suspension of sodium cyanate (0.14 g, 2.20 mmol) in dry acetonitrile (1 ml) and the mixture stirred at room temperature for 4 hours. 5-Bromo-thiazol-2-ylamine hydrobromide (0.26 g, 1.00 mmol) was added and the reaction stirred for 30 minutes. Water (2 ml) and acetic acid (3 drops) were added. The resulting precipitate was filtered and the solid washed with water, cold methanol and diethyl ether. The solid was dried under reduced pressure to give 4-bromo-N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-5-chlorothiophene-2-sulfonamide, 0.29 g (60%), m/e 477.8 (MH−).

Aufarbeitung

  1. stirringthe reaction stirred for 30 minutes
  2. filtrationThe resulting precipitate was filtered
  3. washthe solid washed with water, cold methanol and diethyl ether
  4. customThe solid was dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b7e58246bbc2468bb2c288d11cb2e1de
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868030B2

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