Water → 2-Ureido-benzo[b]thiophene-3-carboxylic Acid Amide

HRID 1594236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594236
[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([NH2:13])=[O:12].ClS([N:18]=[C:19]=[O:20])(=O)=O.O>C(Cl)Cl>[NH:1]([C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([NH2:13])=[O:12])[C:19]([NH2:18])=[O:20]

Komponenten

5

Edukt 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 122835332-Aminobenzo[b]thiophene-3-carboxamide

Produkt 1

HCID 103991682-Ureido-benzo[b]thiophene-3-carboxylic Acid AmideAusbeute 40,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the mixture of 2a (20 mg, 0.104 mmol) in CH2Cl2 (10 mL) was added chlorosulfonyl isocyanate (15 μL, 0.15 mmol). The resultant mixture was stirred at room temperature for 1 h and mixed with water (0.5 mL). Separation via a reverse phase HPLC provided the title compound (10 mg, 40%) as a white solid: MS (ES) m/z 236 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ10.77 (s, 1H), 7.84 (m, 2H), 7.56 (brs, 3H), 7.20 (m, 1H), 7.08 (m, 1H), 6.98 (brs, 1H).

Aufarbeitung

  1. customSeparation via a reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4dbb47368cb74d018b9ff32391be4e3d
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07300952B2

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