2-Aminothiazole → 4-Iodo-N-(thiazol-2-yl)benzenesulfonamide

HRID 77281

Reaktionsgleichung

Reaktionsgleichung von HRID 77281
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH:7]1[C:12]([S:13](Cl)(=[O:15])=[O:14])=[CH:11][CH:10]=[C:9]([I:17])[CH:8]=1.Cl.S1C(N)=NC=N1>N1C=CC=CC=1>[I:17][C:9]1[CH:8]=[CH:7][C:12]([S:13]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)(=[O:15])=[O:14])=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 21552-AminothiazoleHCID 73994-Iodobenzenesulfonyl chlorideHCID 220145431,2,4-Thiadiazol-5-amine--hydrogen chloride (1/1)

Produkt 1

HCID 10193184-Iodo-N-(thiazol-2-yl)benzenesulfonamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a stirring solution of 2-aminothiazole (13.2 g, 132.2 mmol) and pyridine (20 mL) under N2, at 0° C., was added pipsyl chloride (20.0 g, 55.1 mmol). The mixture was stirred at ambient temperature for 17 hours. CH2Cl2/MeOH-2/1 (100 mL) was added. The mixture was filtered and the filtrate was purified via silica gel chromatography using 5% MeOH in CH2Cl2. The solid was triturated with CH2Cl2 to obtain the desired sulfonamide as a white solid (8.4 g, 20.9 mmol, 38% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.83 (s, 1H), 7.94-7.90 (m, 2H), 7.57-7.54 (m, 2H), 7.26 (d, J=4.6 Hz, 1H), 6.86 (d, J=4.6 Hz, 1H).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe filtrate was purified via silica gel chromatography
  3. customThe solid was triturated with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-9b26e25ad7924231ad93b93669dc473c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841282B2

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