HCID 12221603, compound → HCID 23353156, compound

HRID 2379320Notes

Reaction equation

HRID 2379320 reaction equation
[CH:1]([C:4]([NH:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)(=[O:9])=[O:8])=[O:5])([CH3:3])[CH3:2]>C(O)C.[Pd].O>[CH:1]([C:4]([NH:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)(=[O:9])=[O:8])=[O:5])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 12221603HCID 12221603, compound

Product 1

HCID 23353156HCID 23353156, compoundYield 76.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 1-(isopropylcarbonylaminosulphonyl)-3-nitrobenzene (5 g, 18.4 mmol) in ethanol (100 ml) was added 10% palladium on carbon (0.5 g, 10% (w/w)) in water (5 ml). The mixture was hydrogenated at 40 psi for 10 min then the catalyst was filtered off and washed with ethanol. The solvents were evaporated in vacuo to give the title compound (3.4 g, 76%) as a yellow solid. mp 110°-112° C. 1H NMR (360 MHz, D6 -DMSO) δ 0.95 (6H, d, J=6.9 Hz), 2.45 (1H, septet, J=6.9 Hz), 5.63 (2H, br s), 6.79 (1H, ddd, J=8.0, 2.3 and 0.8 Hz), 6.96 (1H, ddd, J=7.6, 1.7 and 0.8 Hz), 7.09 (1H, dd, J=2.0 and 2.0 Hz), 7.20 (1 H, dd, J=7.9 and 7.9 Hz), 11.79 (1H, brs).

Workup

  1. filtrationthe catalyst was filtered off
  2. washwashed with ethanol
  3. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-3fc1f114f45a4945b9f339e3a96b9c51
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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