Pyridine → 5-Methyl-thiophene-2-carboxylic acid (7-bromo-4-methoxybenzothiazol-2-yl)-amide

HRID 2308466

Reaktionsgleichung

Reaktionsgleichung von HRID 2308466
[NH2:1][C:2]1[S:3][C:4]2[C:10]([Br:11])=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[C:5]=2[N:6]=1.N1C=CC=CC=1.[CH3:20][C:21]1[S:25][C:24]([C:26](Cl)=[O:27])=[CH:23][CH:22]=1>ClCCl>[Br:11][C:10]1[C:4]2[S:3][C:2]([NH:1][C:26]([C:24]3[S:25][C:21]([CH3:20])=[CH:22][CH:23]=3)=[O:27])=[N:6][C:5]=2[C:7]([O:12][CH3:13])=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 27600835-Methylthiophene-2-carbonyl chlorideHCID 222832007-Bromo-4-methoxy-1,3-benzothiazol-2-amine

Produkt 1

HCID 865849105-Methyl-thiophene-2-carboxylic acid (7-bromo-4-methoxybenzothiazol-2-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Amino-7-bromo-4-methoxybenzothiazol (2.33 g, 9 mmol) is dissolved in dichloromethane (100 ml) and at 0° C. treated with pyridine (2.2 ml, 27 mmol) and 5-methyl-thiophene-2-carbonyl chloride (2.2 g, 13.5 mmol). The reaction mixture is allowed to warm to room temperature and after stirring for additional 18 h quenched with water (100 ml). After separation of the phases, the aqueous phases are extracted twice with ethyl acetate. The combined organic layers are then washed with brine, dried and avaporated to dryness. Flash chromatography on silica (eluent ethyl acetate/cyclohexane 1:1 to 4:1) and final recrystallization from ethyl acetate affords the product as off-white solid. (34 mg, 69%). MS: m/e=384 (M+).

Aufarbeitung

  1. customquenched with water (100 ml)
  2. customAfter separation of the phases
  3. extractionthe aqueous phases are extracted twice with ethyl acetate
  4. washThe combined organic layers are then washed with brine
  5. customdried
  6. customFlash chromatography on silica (eluent ethyl acetate/cyclohexane 1:1 to 4:1) and final recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8b65a03d0e7840c781f37db88e0ef02b
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06835732B2

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