Methanol → HCID 16781252, compound

HRID 1787996Notes

Reaction equation

HRID 1787996 reaction equation
[CH:1]([N:4]([CH3:17])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-])=O)(=[O:7])=[O:6])([CH3:3])[CH3:2].CO.O.NN>[Ni].ClCCl.C(OCC)(=O)C>[CH:1]([N:4]([CH3:17])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14])(=[O:7])=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 57434735HCID 57434735, compound

Product 1

HCID 16781252HCID 16781252, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21226138Dichloromethane ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

A 250 mL round bottom flask was equipped with a magnetic stirrer and an ice bath. The flask was charged with N-isopropyl-N-methyl-2-nitrobenzenesulfonamide (9.21 mmol), followed by methanol (100 mL). The solution was cooled to 0° C. Hydrazine monohydrate (92.1 mmol) was added, followed by Raney nickel (catalytic amount). After 5 hours TLC (9:1 dichloromethane/ethyl acetate) indicated that the reaction was complete. The reaction was filtered through celite and the catalyst recovered to a separate waste stream. The methanol was removed under reduced pressure and water (100 mL) added. The aqueous solution was extracted with ethyl acetate (100 mL), dried (Na2SO4), filtered, and the solvent removed under vacuum. The resultant yellow oil was purified by silica gel chromatography (1.5″ millimeter×18″ length, 9:1 dichloromethane/ethyl acetate). Fractions containing the desired product were combined and the solvent removed under vacuum to yield N-(isopropyl)-N-(methyl)-2-amino benzene sulfonamide as a clear yellow oil. 2.21 g, (81%). LC/MS: m/z 229.4 [C10H16N2O2S+H]+. 1H-NMR (CDCl3): δ 1.04-1.06 (d, 6H, J=6.7 Hz); 2.73 (s, 3H); 4.15-4.24 (m, 1H, J=6.7 Hz); 4.95 (b, 2H); 6.68-6.78 (m, 2H); 7.24-7.29 (t, 1H, J=7.7 Hz); 7.62-7.65 (d, 1H, J=8.0 Hz)

Workup

  1. customA 250 mL round bottom flask was equipped with a magnetic stirrer and an ice bath
  2. filtrationThe reaction was filtered through celite
  3. customthe catalyst recovered to a separate waste stream
  4. customThe methanol was removed under reduced pressure and water (100 mL)
  5. additionadded
  6. extractionThe aqueous solution was extracted with ethyl acetate (100 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvent removed under vacuum
  10. customThe resultant yellow oil was purified by silica gel chromatography (1.5″ millimeter×18″ length, 9:1 dichloromethane/ethyl acetate)
  11. additionFractions containing the desired product
  12. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-2ff66529c7c44f218e58a3d166c2114b
Source dataset
uspto-grants-2009_03
Patent number
US07511133B2

Reaction notes

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