Ethyl Acetate → 3,4-diamino-N-(cyclopentyloxy)benzenesulfonamide

HRID 29155Notes

Reaction equation

HRID 29155 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:18]([O-])=O.C(OCC)(=O)C>[Pd].C(O)C>[NH2:18][C:3]1[CH:4]=[C:5]([S:8]([NH:11][O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:9])=[O:10])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 229971904-amino-N-(cyclopentyloxy)-3-nitrobenzenesulfonamide

Product 1

HCID 229971823,4-diamino-N-(cyclopentyloxy)benzenesulfonamideYield 100.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-amino-N-(cyclopentyloxy)-3-nitrobenzenesulfonamide (4.50 g, 14.95 mmol) in 1:1 ethyl acetate:ethanol (150 mL) was combined with 5% Pd on barium sulfate and reduced under a hydrogen atmosphere over 72 hours. The reaction mixture was filtered through a pad of diatomaceous earth and evaporated in vacuo to a residue which crystallized on standing. The solid was slurried in hexane, filtered and dried under high vacuum to provide 3,4-diamino-N-(cyclopentyloxy)benzenesulfonamide (4.086 g, 100%) as a light brown solid H1-NMR (dimethylsulfoxide-D6): 1.61 (m, 8H), 4.37 (m, 1H), 4.90 (b, 2H), 5.38 (b, 2H), 6.57 (d, 1H), 6.88 (m, 1H), 6.96 (d, 1H), 9.64 (s, 1H). MS(ESI): 272(M+H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. customevaporated in vacuo to a residue which
  3. customcrystallized
  4. filtrationfiltered
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-13dbb797a45142c6b9b7401d41f37a77
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Reaction notes

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