Butyl bromide → 2-(2-(Butylthio)2-methylpropylamino]-1-(2-mercapto-2-methylpropylamino)benzene

HRID 1090047Notes

Reaction equation

HRID 1090047 reaction equation
[SH:1][C:2]([CH3:18])([CH3:17])[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH2:12][C:13]([CH3:16])([SH:15])[CH3:14].Br[CH2:20][CH2:21][CH2:22][CH3:23].[H-].[Na+].CCCCCC>O1CCCC1.C(OCC)(=O)C>[CH2:20]([S:1][C:2]([CH3:18])([CH3:17])[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH2:12][C:13]([SH:15])([CH3:16])[CH3:14])[CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 8002Butyl bromideHCID 8058HexaneHCID 24758Sodium hydrideHCID 99258511,2-Bis (2-Mercapto-2-methylpropylamino)benzene

Product 1

HCID 100268592-(2-(Butylthio)2-methylpropylamino]-1-(2-mercapto-2-methylpropylamino)benzeneYield 23%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,2-Bis (2-mercapto-2-methylpropylamino)benzene (0.17 g, 6.1×10-4 mol, 120 M%) and 0.07 g (5.1×10-4 mol, 100 M%) 1- bromobutane were dissolved in 25 ml tetrahydrofuran (freshly distilled over Na). Sodium hydride (0.03 g, 6.25×10-4 mol, 102 M%) was then added. The mixture was stirred at room temperature under nitrogen for 3 hours. The reaction mixture was worked up as in Example 40. The product was isolated by radial chromatography on 1 mm silica plate, using hexane: ethyl acetate as the eluting solvent, giving 40 mg (23% yield) 2-(2-butylthio-2-methylpropylamino]-1-(2-mercapto-2-methylpropylamino)benzene as a yellow oil.

Workup

  1. distillationfreshly distilled over Na)
  2. customThe product was isolated by radial chromatography on 1 mm silica plate

Sources & evidence

ORD record
ord-f3aad7585095476db321728c368faf1a
Source dataset
uspto-grants-1992_01
Patent number
US05080884

Reaction notes

Loading…