Acetic Acid → 1-[2-(3-Butenylthio)-2-methylpropylamino]-2-(2-mercapto-2-methylpropylamino)benzene

HRID 1494701Notes

Reaction equation

HRID 1494701 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]([SH:13])([CH3:12])[CH3:11].[CH2:14]([S:18][C:19]([CH3:23])([CH3:22])[CH:20]=O)[CH2:15][CH:16]=[CH2:17].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:14]([S:18][C:19]([CH3:23])([CH3:22])[CH2:20][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]([SH:13])([CH3:11])[CH3:12])[CH2:15][CH:16]=[CH2:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 100129272-Amino-1-(2-mercapto-2-methylpropylamino)benzeneHCID 104645802-(3-Butenylthio)-2-methylpropanal

Product 1

HCID 100494231-[2-(3-Butenylthio)-2-methylpropylamino]-2-(2-mercapto-2-methylpropylamino)benzeneYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Amino-1-(2-mercapto-2-methylpropylamino)benzene (3.5 g, 1.78×10-2 mol, 100 M %) and 2-(3-butenylthio)-2methylpropanal (4.23 g, 2.67×10-2 mol, 150 M %) were dissolved in 200 ml methanol. Glacial acetic acid (2.05 ml, 3.56×10-2 mol, 200 M %) and sodium cyanoborohydride (3.36 g, 5.35×10-2 mol, 300 M %) were then added. After 17 hours, the reaction was quenched by the addition of 100 ml 0.5N HCl. The acidic solution was then extracted with 2×100 ml diethyl ether. The combined organic extracts were washed with 100 ml saturated NaHCO3, followed by 100 ml saturated NaCl. The ether layer was then dried over anhydrous Na2SO4. The solvent was removed on the rotary evaporator, and the residue was purified by filtration through a 600 ml sintered-glass funnel silica bed, using 90% hexane/diethyl ether as the eluting solvent, to give 5 g (84% yield) 1-[2-(3-butenylthio)-2-methylpropylamino]-2-(2-mercapto-2-methylpropylamino)benzene as a yellow oil.

Workup

  1. customthe reaction was quenched by the addition of 100 ml 0.5N HCl
  2. extractionThe acidic solution was then extracted with 2×100 ml diethyl ether
  3. washThe combined organic extracts were washed with 100 ml saturated NaHCO3
  4. dry with materialThe ether layer was then dried over anhydrous Na2SO4
  5. customThe solvent was removed on the rotary evaporator
  6. filtrationthe residue was purified by filtration through a 600 ml sintered-glass funnel silica bed

Sources & evidence

ORD record
ord-3b94da8b57f24345b640cb52c90db525
Source dataset
uspto-grants-1991_06
Patent number
US05026913

Reaction notes

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