Water → Biphenyl-4-sulfonic acid [2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(4-hydroxy-butyl)-amide

HRID 2425124Notes

Reaction equation

HRID 2425124 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].[C:22]([Si:26]([O:39][CH2:40][CH2:41]I)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:25])([CH3:24])[CH3:23].O>CN(C=O)C>[C:22]([Si:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[O:39][CH2:40][CH2:41][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][OH:1])[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])([CH3:23])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 11269862Tert-butyl(2-iodoethoxy)diphenylsilaneHCID 16094717N-(4-Hydroxybutyl)[1,1'-biphenyl]-4-sulfonamide

Product 1

HCID 59728311Biphenyl-4-sulfonic acid [2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(4-hydroxy-butyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Biphenyl-4-sulfonic acid-(4-hydroxybutyl)-amide (1 g) and tert-butyl-(2-iodo-ethoxy) diphenyl silane (2 g) were heated in DMF (30 mL) for 3 hours at 60° C. The resultant mixture was poured into water and extracted with dichloromethane. Evaporation and column chromatography (petrol/ethyl acetate) gave the title compound as an amorphous solid. δC (CDCl3, 62.9 MHz): 19.2, 25.1, 26.8, 29.5, 49.3, 49.8, 62.4, 62.9, 127.3, 127.6, 127.7, 127.8, 128.5, 129.1, 129.9, 133.2, 135.6, 138.4, 139.4 and 145.3.

Workup

  1. extractionextracted with dichloromethane
  2. customEvaporation and column chromatography (petrol/ethyl acetate)

Sources & evidence

ORD record
ord-736f69d73cd14bb1bb13ec7b373d5dea
Source dataset
uspto-grants-2011_06
Patent number
US07964643B2

Reaction notes

Loading…