Hydrochloric Acid → 1-(2-Allylthio-2-methylpropylamino)-2-(2-mercapto-2-methylpropylamino]benzene

HRID 1494700Notes

Reaction equation

HRID 1494700 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:17][C:18]([CH3:22])([CH3:21])[CH:19]=O)[CH:15]=[CH2:16].C([BH3-])#N.[Na+].Cl>CO.C(O)(=O)C>[CH2:14]([S:17][C:18]([CH3:22])([CH3:21])[CH2:19][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])[CH:15]=[CH2:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 100129272-Amino-1-(2-mercapto-2-methylpropylamino)benzeneHCID 102409332-(Allylthio)-2-methylpropanal

Product 1

HCID 100716871-(2-Allylthio-2-methylpropylamino)-2-(2-mercapto-2-methylpropylamino]benzeneYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

2-Amino-1-(2-mercapto-2-methylpropylamino)benzene (3.5 g, 1.78×10-2 mol) and 2-(allylthio)-2-methylpropanal (3.85 g, 2.67×10-2 mol, 150 M %) were dissolved in 200 ml methanol. Glacial acetic acid (2.05 ml, 3.56×10-2, 200 M %) and sodium cyanoborohydride (3.36 g, 5.35×10-2 % mol, 300 M %) were then added. The reaction was stirred at room temperature for 18 hr, then 100 ml 0.50.5 M HCl was added and the mixture was extracted with 2×100 ml diethyl ether. The combined organic extracts were washed with 100 ml saturated NaHCO3, then with 100 ml saturated NaCl. The ether layer was dried over anhydrous Na2SO4, and the solvent was removed on the rotary evaporator. The crude product (6.7 g) was purified by filtration through a 600 ml sintered glass funnel filled silica bed, using 95% hexane/diethyl ether as the eluting solvent to give 4 g (70% yield) of 1-(2-allylthio-2-methylpropylamino)-2-(2-mercapto-2-methylpropylamino]benzene as a yellow oil.

Workup

  1. extractionthe mixture was extracted with 2×100 ml diethyl ether
  2. washThe combined organic extracts were washed with 100 ml saturated NaHCO3
  3. dry with materialThe ether layer was dried over anhydrous Na2SO4
  4. customthe solvent was removed on the rotary evaporator
  5. filtrationThe crude product (6.7 g) was purified by filtration through a 600 ml sintered glass funnel
  6. additionfilled silica bed

Sources & evidence

ORD record
ord-428abfa491184910bf57fa8d2a0add40
Source dataset
uspto-grants-1991_06
Patent number
US05026913

Reaction notes

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