Hydrochloric Acid → 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-(2-(methylsulfinyl)ethoxy)benzamide

HRID 1382961

Reaktionsgleichung

Reaktionsgleichung von HRID 1382961
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:19][CH2:20][CH2:21][S:22][CH3:23])[CH:3]=1.Cl.I([O-])(=O)(=O)=[O:26].[Na+].[OH-].[Na+]>O.C(Cl)Cl>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])=[C:4]([O:19][CH2:20][CH2:21][S:22]([CH3:23])=[O:26])[CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 124098Metoclopramide sulfideHCID 23667635Sodium periodate

Produkt 1

HCID 98229474-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-(2-(methylsulfinyl)ethoxy)benzamideAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-amino-5-chloro-N-[2(diethylaxino)ethyl]-2-[2-(methylthio)ethoxy]benzamide (1.0 g, 2.28 mmoles) (prepared in Example 20) and 1.4N HCl solution (3.97 ml, 5.56 mmoles) in 15 ml of H2O at 0°-5°, was added sodium metaperiodate (0.625 g, 2.92 mmoles). The mixture, which soon began to darken, was stirred at 0°-5° for 2 hours. The mixture was then diluted to 50 ml and made alkaline (pH=12) with NaOH solution. Methylene chloride (50 ml) was added, the mixture was shaken well, and the layers were separated. The aqueous layer was extracted with 3 portions of methylene cloride and the combined organic solutions were dried (anhydrous MgSO4) and evaporated. A dark oil (0.96 g) which solidified upon standing was obtained. The crude product was flash chromatographed on silica, eluting with CH2CL2 :CH3OH:NH4OH, 80:20:0.5. Appropriate fractions were combined and evaporated to give 0.80 g (77%) of the title compound as a yellow resin which crystallized upon standing, mp. 110°-114°.

Aufarbeitung

  1. additionThe mixture was then diluted to 50 ml
  2. stirringthe mixture was shaken well
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with 3 portions of methylene cloride
  5. dry with materialthe combined organic solutions were dried (anhydrous MgSO4)
  6. customevaporated
  7. customupon standing was obtained
  8. customchromatographed on silica
  9. washeluting with CH2CL2
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-fd5237de39754434834be192dee28c9a
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04808624

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