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Acetic Acid → 6-chloro-2,3-dihydro-3-oxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide hydrochloride

HRID 2164541
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2164541
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:19])[N:7]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:8]2=O)=[CH:4][C:3]=1[S:20]([NH2:23])(=[O:22])=[O:21].O=C1C2C(=CC=CC=2)C(=O)N1.C(O)(=O)C.Cl>CN(C)C=O.[Zn].C(O)(=O)C.[Zn]>[ClH:1].[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:19])[N:7]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:8]2)=[CH:4][C:3]=1[S:20]([NH2:23])(=[O:22])=[O:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 6809Phthalimide2×HCID 134731836-Chloro-2,3-dihydro-1,3-dioxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide

Produkt 1

HCID 204048526-chloro-2,3-dihydro-3-oxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysator2×
HCID 57475673ZINC acetic acidKatalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Zinc-acetic acid reduction of 6-chloro-2,3-dihydro-1,3-dioxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide. Zinc dust (0.5 mole) is added in one portion to the 1,3-dioxoisoindole (0.1 mole) of part (a) in 800 ml. of acetic acid. The reaction mixture is stirred at room temperature for 1.0 hr. and then heated to reflux for a 6 hr. period during which time additional 9.0 g. portions of zinc are added at the end of 3, 4, and 5 hr., respectively. After stirring overnight, the reaction mixture is filtered and the filtrate concentrated to dryness under reduced pressure with additional water added to the residue and removed in vacuo to remove traces of acetic acid. Residual material is slurried in water, filtered, and the filtrate concentrated to dryness. Residual material is stirred with saturated sodium bicarbonate solution and an immiscible organic solvent such as hot ethyl acetate. The organic fraction is separated, dried over MgSO4 and concentrated to provide the product as the free base. The free base taken up in dimethylformamide and acidified with ethanolic hydrogen chloride affords 6-chloro-2,3-dihydro-3-oxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide hydrochloride.

Aufarbeitung

  1. temperatureand then heated
  2. temperatureto reflux for a 6 hr
  3. stirringAfter stirring overnight
  4. filtrationthe reaction mixture is filtered
  5. concentrationthe filtrate concentrated to dryness under reduced pressure with additional water
  6. additionadded to the residue
  7. customremoved in vacuo
  8. customto remove traces of acetic acid
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated to dryness
  11. stirringResidual material is stirred with saturated sodium bicarbonate solution
  12. customThe organic fraction is separated
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated
  15. customto provide the product as the free base

Quellen und Nachweise

ORD-Eintrag
ord-9415240d1fc74991ab09c1626e1fa663
Quelldatensatz
uspto-grants-1985_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04505911

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