1,4-Dioxane → HCID 19605502, compound

HRID 1603592Notes

Reaction equation

HRID 1603592 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([Br:18])[N:3]=1.[CH3:19][NH:20][CH2:21][CH2:22][CH2:23]N.O1CCOC[CH2:26]1>>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:6]2[CH:7]=[C:2]([NH:3][CH2:23][CH2:22][CH2:21][NH:20][CH3:19])[CH:26]=[C:4]([Br:18])[CH:5]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 80511N-Methyl-1,3-propanediamineHCID 110146744-(2,6-dibromopyridin-4-yl)sulfonylaniline

Product 1

HCID 19605502HCID 19605502, compoundYield 42%

Procedure

0.20 g (0.00051 mol) of 4-(2,6-dibromopyridine-4-sulphonyl)-phenylamine was dissolved in 10 ml of dioxane and treated with 5.1 ml of 3-methylaminopropylamine. The mixture was stirred at room temperature for 2 hrs., the solvent was removed and the residue was chromatographed twice on silica gel, firstly with 20% methanol in dichloromethane and then with 10% methanol in dichloromethane. There was obtained 0.085 g (42%) of N-[3-(4-aminobenzenesulphonyl)-5-bromophenyl]-N'-methylpropane-1,3-diamine as a pale yellow, amorphous solid; MS (ISP): me/e=401, 399 (C15H20BrN4O2S+).

Workup

  1. custom, the solvent was removed
  2. customthe residue was chromatographed twice on silica gel, firstly with 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-0e9ff5e898cd42d0adf401b6db833b07
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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