Formic Acid → N,N-Dimethyl-2-aminosulfonyl-4-formamidobenzamide

HRID 505949

Reaktionsgleichung

Reaktionsgleichung von HRID 505949
[CH3:1][N:2]([CH3:18])[C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[S:13]([NH2:16])(=[O:15])=[O:14].[CH:19](O)=[O:20]>[O-][Mo]([O-])(=O)=O.[Na+].[Na+].[Pd]>[CH3:1][N:2]([CH3:18])[C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:19]=[O:20])=[CH:6][C:5]=1[S:13]([NH2:16])(=[O:15])=[O:14]

Komponenten

5

Edukt 2

HCID 284Formic AcidHCID 22066001N,N-Dimethyl-4-nitro-2-sulfamoylbenzamide

Produkt 1

HCID 15240549N,N-Dimethyl-2-aminosulfonyl-4-formamidobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 61424Sodium MolybdateKatalysator

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A suspension of 40 g N,N-Dimethyl 2-aminosulfonyl-4-nitrobenzamide (VIII), sodium molybdate (0.08 g) and Pd/C (3 g, 5%, 50% water) in formic acid (200 ml) was hydrogenated at 50° C. and 40 bar for 7 hours. The catalyst was then filtered and washed with formic acid (20 ml). The filtrate was concentrated in vacuo and ethyl acetate (200 ml) added. After stirring for 2 hours at 20° C. the product was filtered, the filtrate concentrated and re-filtered. The combined solids were washed with ethyl acetate (20 ml) and dries at 50° C./50 mbar. Yield: 35.3 g (=84.3%), 94.1% w/w, mp.: 192-193° C.

Aufarbeitung

  1. customwas hydrogenated at 50° C.
  2. filtrationThe catalyst was then filtered
  3. washwashed with formic acid (20 ml)
  4. concentrationThe filtrate was concentrated in vacuo and ethyl acetate (200 ml)
  5. additionadded
  6. filtrationwas filtered
  7. concentrationthe filtrate concentrated
  8. filtrationre-filtered
  9. washThe combined solids were washed with ethyl acetate (20 ml) and dries at 50° C./50 mbar

Quellen und Nachweise

ORD-Eintrag
ord-2859279ccf80494dbc0d185f567de2f3
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781611B2

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