Water → Biphenyl-4-sulfonic acid-(4-hydroxybutyl)-methyl-amide

HRID 2425117Notes

Reaction equation

HRID 2425117 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].[CH3:22]I.O>CN(C)C=O>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH3:22])[S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 16094717N-(4-Hydroxybutyl)[1,1'-biphenyl]-4-sulfonamide

Product 1

HCID 11594884Biphenyl-4-sulfonic acid-(4-hydroxybutyl)-methyl-amideYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from biphenyl-4-sulfonic acid-(4-hydroxybutyl)-amide (0.4 g), methyl iodide (0.2 mL) and K2CO2 (0.5 g) in dimethylformamide (20 mL). The mixture was stirred at room temperature for 4 hours, poured into water and extracted with diethyl ether. The organic phase was repeatedly washed with water and evaporated to give the title compound as a white solid (80%). δC (DMSO, 62.9 MHz): 23.7, 29.5, 34.5, 49.6, 60.2, 127.1, 127.2, 127.6, 128.6, 129.2, 135.8, 138.4 and 144.3. δH (DMSO, 250 MHz): 1.45 (4H, m), 2.68 (3H, s), 2.97 (2H, t, J 7.0), 3.40 (2H, m), 7.49 (3H, m), 7.75 (2H, d, J 7.0), 7.83 (2H, d, J 8.5) and 7.91 (2H, d, J 8.2).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was repeatedly washed with water
  3. customevaporated

Sources & evidence

ORD record
ord-d31c28ff80334387957f461bb2b4c274
Source dataset
uspto-grants-2011_06
Patent number
US07964643B2

Reaction notes

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