Methyl iodide → 1-[2-Methylthio-2-methylpropylamino]-2-(2-mercapto-2-methylpropylamino)benzene

HRID 1494705Notes

Reaction equation

HRID 1494705 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].[H-].[Na+].[CH3:21]I>O1CCCC1>[CH3:21][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]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 99258511,2-Bis (2-Mercapto-2-methylpropylamino)benzene

Product 1

HCID 199142591-[2-Methylthio-2-methylpropylamino]-2-(2-mercapto-2-methylpropylamino)benzeneYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,2-Bis (2-Mercapto-2-methylpropylamino)benzene (0.47 g, 1.69×10-3 mol), and 0.09 g (1.85×10-3 mol, 110 M %) sodium hydride were dissolved in 25 ml tetrahydrofuran. Methyl iodide (0.080 ml, 1.27×10-3 mol, 75 M %) was added, and the mixture was stirred under nitrogen for 1 hour. The excess hydride was destroyed by the slow addition of 10 ml 0.5 M HCl. The mixture was shaken with a mixture of 100 ml ether and 100 ml 0.5 N HCl. The aqueous layer was extracted with an additional 50 ml portion of ether, and the combined ether layers were washed with 100 ml saturated NaCl. The ether layer was then dried over anhydrous Na2SO4. Rotary evaporation yielded 0.30 g (94% yield) of 1-[2-methylthio-2-methylpropylamino]-2-(2-mercapto-2-methylpropylamino)benzene as a yellow oil. Isolation was performed by radial chromatograph on a 1 mm silica plate, using petroleum ether: ethyl acetate-80:20 as the eluting solvent to give yielding a mixture of the 1-[2-methylthio-2-methylpropyl- amino]-2-(2-mercapto-2-methylpropylamino)benzene, S,S'-dimethyl, and the dithiol starting material.

Workup

  1. customThe excess hydride was destroyed by the slow addition of 10 ml 0.5 M HCl
  2. stirringThe mixture was shaken with a mixture of 100 ml ether and 100 ml 0.5 N HCl
  3. extractionThe aqueous layer was extracted with an additional 50 ml portion of ether
  4. washthe combined ether layers were washed with 100 ml saturated NaCl
  5. dry with materialThe ether layer was then dried over anhydrous Na2SO4
  6. customRotary evaporation

Sources & evidence

ORD record
ord-9b7a53a8ea794fb395f39075c6933d4e
Source dataset
uspto-grants-1991_06
Patent number
US05026913

Reaction notes

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