Pyridine → HCID 57920370, Verbindung

HRID 1511497

Reaktionsgleichung

Reaktionsgleichung von HRID 1511497
Cl.[CH3:2][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=2[S:6][C:7]=1[NH2:8].N1C=CC=CC=1.Cl[S:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C1COCC1.CCOC(C)=O>[CH3:2][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=2[S:6][C:7]=1[NH:8][S:20]([C:23]1[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:30][CH:31]=1)(=[O:22])=[O:21]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 823854-(Chlorosulfonyl)benzoic acidHCID 567239383-Methyl-1-benzothiophen-2-amine hydrochloride

Produkt 1

HCID 57920370HCID 57920370, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A 12-L 4-neck flask equipped with an overhead mechanical stirrer, N2 inlet/outlet adapter, and thermocouple was charged with THF (3.26 L) and 3-methylbenzo[b]thiophen-2-amine hydrochloride (326 g, 1.6 mol) followed by pyridine (265 mL, 3.3 mol). The resulting mixture was cooled to 5° C. using a ice bath, to which was added a solution of 4-(chlorosulfonyl)benzoic acid (396 g, 1.8 mol) dissolved in THF (2.44 L), drop-wise. The resulting mixture was allowed to stir at ambient temperature for 72 h, was then diluted with EtOAc (4 L), washed with 1N HCl (1 L), brine (1 L), the organic layer dried over Na2SO4, filtered and evaporated under reduced pressure to yield a residue. The residue was purified by triturating with EtOAc/heptane (1:1/1 L). The resulting slurry was filtered, washed with heptane (2×250 mL) and dried in a vacuum oven at 40° C. for 18 h to yield N-(3-methylbenzo[b]thiophen-2-yl)-4-carboxy-benzenesulfonamide as a white solid. 1H-NMR (DMSO-d6) δ13.51 (br s, 1H), 10.65 (br s, 1H), 8.12 (d, 2H), 7.86 (d, 2H), 7.83-7.79 (m, 1H), 7.66-7.63 (m, 1H), 7.37-7.33 (m, 1H), 2.03 (s, 3H).

Aufarbeitung

  1. customA 12-L 4-neck flask equipped with an overhead mechanical stirrer, N2 inlet/outlet adapter
  2. washwashed with 1N HCl (1 L), brine (1 L)
  3. dry with materialthe organic layer dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto yield a residue
  7. customThe residue was purified
  8. customby triturating with EtOAc/heptane (1:1/1 L)
  9. filtrationThe resulting slurry was filtered
  10. washwashed with heptane (2×250 mL)
  11. customdried in a vacuum oven at 40° C. for 18 h

Quellen und Nachweise

ORD-Eintrag
ord-465170dadb68410f90dd30b5269cd923
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08216547B2

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