HCID 22326785, compound → Benzenesulfonamide, 4-amino-N-(cyclopropylmethyl)-

HRID 495375Notes

Reaction equation

HRID 495375 reaction equation
[CH:1]1([CH2:4][NH:5][S:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:3][CH2:2]1>C(O)C.[Pd]>[CH:1]1([CH2:4][NH:5][S:6]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 22326785HCID 22326785, compound

Product 1

HCID 16788379Benzenesulfonamide, 4-amino-N-(cyclopropylmethyl)-Yield 7.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-[N-(Cyclopropylmethyl)sulphamoyl]nitrobenzene (Method 53; 12.58 g) was reduced by hydrogenation in ethanol (300 ml) over 10% palladium on carbon (1 g) at 3 bar pressure. The catalyst was removed by filtration and the volatiles evaporated. 2 g of this crude product was purified by chromatography eluting with DCM increasing in polarity to 10% MeOH/DCM to give the title compound (850 mg). NMR: 0.08 (m, 2H), 0.25 (m, 2H), 0.83 (m, 1H, 2.80 (t, 2H), 4.15 (br s, 2H), 4.50 (br t, 1H), 6.65 (d, 2H), 7.62 (d, 2H); m/z: 226.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe volatiles evaporated
  3. custom2 g of this crude product was purified by chromatography
  4. washeluting with DCM increasing in polarity to 10% MeOH/DCM

Sources & evidence

ORD record
ord-7a0007494a0a4b6ba40b7426dfd2f380
Source dataset
uspto-grants-2005_09
Patent number
US06939872B2

Reaction notes

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