p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 1164324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1164324
S=C1C2C=CC=C3C=2C(=CC=C3)N1CC(O)=O.NC(O)C.O.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>C1C=CC=CC=1>[CH3:33][C:23]1[CH:24]=[CH:25][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:27][CH:28]=1

Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 522583Acetaldehyde ammoniaHCID 3069842Benz(cd)indole-1(2H)-acetic acid, 2-thioxo-

Produkt 1

HCID 6101p-Toluenesulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A suspension of 2-thioxo-benz[cd]indole-1(2H)-acetic acid (1.0 g, 4.11 mmol, described in Example 6) aminoethanol (0.5 g, 0.49 mL, 8.22 mmol) and p-toluenesulfonic acid hydrate (1.88 g, 9.86 mmol) in benzene (50 mL) was refluxed for 48 hr with stirring in a Soxhlet apparatus containing a thimble filled with 3A molecular sieves. The mixture was evaporated to dryness, and the residue was triturated with cold water (50 mL). The precipitate was collected by filtration, washed with diethyl ether (50 mL), and crystallized from water to give the 4-methylphenylsulfonic acid salt of the title compound (1.0 g): Anal. Calcd for C15H14N2O2S.C7H8O3S: C, 57.63% H, 4.84% N, 6.11% and Found: C, 57.58% H, 4.94% N, 6.23%; IR (mineral oil) 2900, 1740, 1375, and 11700 cm-1 ; UV max (methanol) 342 (ε3400), 310 (6700), 304 (6740), 267 (27,900), 259 (21,580), and 218 nm (26,210); NMR (DMSO-d6)ε 2.25 (s, 3H), 3.12 (t, 2H), 4.32 (t, 2H), 5.3 (s, 2H), 7.7 (m, 10H), and 7.9 (s, 3H).

Aufarbeitung

  1. temperaturewas refluxed for 48 hr
  2. additioncontaining a thimble
  3. customThe mixture was evaporated to dryness
  4. customthe residue was triturated with cold water (50 mL)
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with diethyl ether (50 mL)
  7. customcrystallized from water

Quellen und Nachweise

ORD-Eintrag
ord-189ad8fc91614b02bd36873957e31cb7
Quelldatensatz
uspto-grants-1983_01
Patentnummer
US04369188

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