Ammonia → 7-Mesitylenesulfonyl-1,7,13-triazatridecane

HRID 1978295Notes

Reaction equation

HRID 1978295 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][N:7]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25])[S:8]([C:11]1[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=1[CH3:19])(=[O:10])=[O:9])#[N:2].N.[H][H].[NH4+].[OH-:30]>[Ni].CO>[NH4+:2].[OH-:9].[CH3:23][CH2:24][OH:30].[C:12]1([CH3:19])[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:11]=1[S:8]([N:7]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:1][NH2:2])(=[O:9])=[O:10]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 10832449N,N-Bis(4-cyanobutyl)mesitylenesulfonamideHCID 178418361HCID 178418361, compound

Product 2

HCID 107853557-Mesitylenesulfonyl-1,7,13-triazatridecaneYield 98%HCID 22731726Ethanol ammonium hydroxideYield 5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel (W-2 grade, 2.9 g) and 39 (5.69 g, 15.8 mmol) in concentrated NH4OH (10 mL) and CH3OH (60 mL) were saturated with NH3 as 41. The mixture was shaken with hydrogen at 50-55 psi in a 200 mL Parr bottle for 42 hours. The suspension was filtered through Celite, and the solvents were removed in vacuo. The residue was passed through a short silica gel column (EtOH then 5% concentrated NH4OH/EtOH) to give 5.71 g (98%) of 42 as a light yellow oil: NMR δ 1.17 (m, 4 H), 1.47 (m, 8 H), 2.27 (s, 3 H), 2.57 (s, 6 H), 2.61 (m, 4 H), 3.13 (t, J=7.5, 4 H), 6.91 (s, 2 H); HRMS calcd. for C19H36N3O2S 370.2528 (M+H), found. 370.2530 (M+H).

Workup

  1. filtrationThe suspension was filtered through Celite
  2. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-f2d97bcf51f5498cba3b36b35c47f158
Source dataset
uspto-grants-2001_05
Patent number
US06235794B1

Reaction notes

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