N-(cyclopentyloxy)-3-nitro-1-benzenesulfonamide → 3-amino-N1-(cyclopentyloxy)-1-benzenesulfonamide

HRID 1166470Notes

Reaction equation

HRID 1166470 reaction equation
[CH:1]1([O:6][NH:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)(=[O:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C(O)C.[Pd]>[NH2:17][C:13]1[CH:12]=[C:11]([S:8]([NH:7][O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:9])=[O:10])[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 22997117N-(cyclopentyloxy)-3-nitro-1-benzenesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 229970363-amino-N1-(cyclopentyloxy)-1-benzenesulfonamideYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-(cyclopentyloxy)-3-nitro-1-benzenesulfonamide (2.98 g, 10.41 mmol) in 50 mL of absolute ethanol was combined with 5 wt % Palladium on barium sulfate (300 mg) and reduced under a balloon of hydrogen gas with vigorous agitation for 18 hours. The mixture was filtered, washed with ethanol, and evaporated in vacuo to a residue. The crude product was purified on flash grade silica gel eluting with 4:1 hexane : ethyl acetate. Fractions containing the product were combined, evaporated in vacuo and dried under vacuum to provide 3-amino-N1-(cyclopentyloxy)-1-benzenesulfonamide (2.67 g, 100%) as an oil. Hl-NMR chloroform-D3): 1.62 (m, 8H), 3.92 (bs, 2H), 4.58 (m, 1H), 6.74 (bs, !H), 6.88 (m, 1H), 7.16 (m, 1H), 7.27 (m, 2H). MS(ESI): 257(MH+).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with ethanol
  3. customevaporated in vacuo to a residue
  4. customThe crude product was purified on flash grade silica gel eluting with 4:1 hexane
  5. additionFractions containing the product
  6. customevaporated in vacuo
  7. customdried under vacuum

Sources & evidence

ORD record
ord-1e2c04737af4416a803144b5ec940e63
Source dataset
uspto-grants-2003_09
Patent number
US06613743B2

Reaction notes

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