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

HRID 505949Notes

Reaction equation

HRID 505949 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 61424Sodium MolybdateCatalyst

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2859279ccf80494dbc0d185f567de2f3
Source dataset
uspto-grants-2010_08
Patent number
US07781611B2

Reaction notes

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