Dichloromethane methanol → 4-Hydroxy-3-n-propylbenzenesulfonamide

HRID 865532Notes

Reaction equation

HRID 865532 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[OH:10])[CH:2]=[CH2:3].[H][H].CO.C(Cl)Cl>C(O)C.[Pd]>[OH:10][C:9]1[CH:8]=[CH:7][C:6]([S:11]([NH2:14])(=[O:12])=[O:13])=[CH:5][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 21226129Dichloromethane methanolHCID 217087083-Allyl-4-hydroxybenzenesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 190804514-Hydroxy-3-n-propylbenzenesulfonamideYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A Parr hydrogenation flask was charged with a solution of 3.04 g (14.30 mmol) of the product of Step A dissolved in 25 mL of ethanol and 0.300 g of a 10% palladium on carbon catalyst was added. The flask was mounted in the hydrogenation apparatus, freed of air, pressurized with hydrogen (40 psig) and shaken for 15 minutes. At the end of this period TLC analysis (3% MeOH-CH2Cl2, 2 elutions) indicated that the reaction was complete and the reaction mixture was filtered and evaporated. The product was dried in vacuo to afford 3.06 g (99%) of the title compound. 1H-NMR (400 MHz, CD3OD, ppm): δ 0.94 (t, J=7.20 Hz, 3H), 1.58-1.68 (m, 2H), 2.01-2.62 (m, 2H), 6.82 (d, J=8.40 Hz, 1H), 7.55 (dd, J=2.40, 8.40 Hz, 1H), 7.60 (d, J=2.40 Hz, 1H). FAB-MS m/e=216 (M+1).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated
  3. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-28e008a02e934ccea8a4bbb05539ff29
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

Loading…