Homoallyl bromide → Biphenyl-4-sulfonic acid-(4-hydroxybutyl)-buten-1-yl-amide

HRID 2425122Notes

Reaction equation

HRID 2425122 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].Br[CH2:23][CH2:24][CH:25]=[CH2:26]>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH:23]=[CH:24][CH2:25][CH3:26])[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

3

Reactant 2

HCID 21241Homoallyl bromideHCID 16094717N-(4-Hydroxybutyl)[1,1'-biphenyl]-4-sulfonamide

Product 1

HCID 67245204Biphenyl-4-sulfonic acid-(4-hydroxybutyl)-buten-1-yl-amide

Procedure

Using a method analogous to that described in Example 4, with biphenyl-4-sulfonic acid-(4-hydroxybutyl)-amide and 4-bromobutene, reacted at 60° C. for 3 hours, the title compound was obtained as a white powder. δC (CDCl3, 62.9 MHz): 25.2, 29.6, 33.4, 47.8, 48.3, 62.4, 117.2, 127.3, 127.6, 127.7, 128.5, 129.1, 134.6, 138.4, 139.3 and 145.3. δH (CDCl3, 250 MHz): 1.58 (4H, m), 2.34 (3H, m), 3.21 (4H, m), 3.66 (2H, t, J 6.1), 5.04 (2H, m), 5.69 (1H, m), 7.46 (3H, m), 7.60 (2H, d, J 7.3), 7.70 (2H, d, J 8.2) and 7.86 (2H, d, J 8.2)

Workup

  1. customreacted at 60° C. for 3 hours

Sources & evidence

ORD record
ord-051b19982cc844c49b93afe4f4706453
Source dataset
uspto-grants-2011_06
Patent number
US07964643B2

Reaction notes

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