HCID 58994407, compound → 2-(4-Amino-phenyl)-ethanesulfonic acid dimethylamide

HRID 1190134Notes

Reaction equation

HRID 1190134 reaction equation
[CH3:1][N:2]([CH3:17])[S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)(=[O:5])=[O:4]>CO.[Pd]>[CH3:17][N:2]([CH3:1])[S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)(=[O:4])=[O:5]

Participants

4

Reactant 1

HCID 58994407HCID 58994407, compound

Product 1

HCID 589943702-(4-Amino-phenyl)-ethanesulfonic acid dimethylamideYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 912 mg (3.53 mmol) of 2-(4-nitro-phenyl)-ethanesulfonic acid dimethylamide (as prepared in the previous step) in MeOH (30 mL) was hydrogenated with 10% Pd/C (Degussa type E101-NE/W, Aldrich, 50% by weight water) at 20 psi H2 at RT for 2 days. The mixture was filtered through Celite, the filter cake was washed with MeOH, and the solvents were evaporated in vacuo. Silica gel chromatography of the residue on a 25-g Varian MegaBond Elut SPE column with 50% EtOAc-hexane afforded 737 mg (91%) of the title compound as a white solid: 1H-NMR (CD3CN; 400 MHz): δ 7.01 (d, 2H, J=8.4 Hz), 6.61 (d, 2H, J=8.4 Hz), 4.06 (br s, 2H), 3.19-3.13 (m, 2H), 2.95-2.88 (m, 2H), 2.84 (s, 6H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed with MeOH
  3. customthe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-87f605f40ab442908890d8e2353f2e61
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

Loading…