Acetic Acid → 2-(2-Mercapto-2-methylpropylamino)-1-[2-(4-pentenylthio)-2-methylpropylamino]-benzene

HRID 1090038Notes

Reaction equation

HRID 1090038 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:19][C:20]([CH3:24])([CH3:23])[CH:21]=O)[CH2:15][CH2:16][CH:17]=[CH2:18].C(O)(=O)C.C([BH3-])#N.[Na+].Cl>CO>[SH:13][C:10]([CH3:11])([CH3:12])[CH2:9][NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH2:21][C:20]([S:19][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])([CH3:24])[CH3:23]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 100129272-Amino-1-(2-mercapto-2-methylpropylamino)benzeneHCID 102412662-(4-Pentenylthio)-2-methylpropanal

Product 1

HCID 100436132-(2-Mercapto-2-methylpropylamino)-1-[2-(4-pentenylthio)-2-methylpropylamino]-benzeneYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Amino-1-(2-mercapto-2-methylpropylamino)benzene (0.155 g, 7/9×10-4 mol) and 0.30 g (1.74×10-3 mol, 220 M%) of 2-(4-pentenylthio)-2-methylpropanal were dissolved in 40 ml methanol. Acetic acid (0.09 ml, 1.59×10-3 mol, 200 M%) was added followed by 0.155 g (2.3×10-3 mol, 300 M%) sodium cyanoborohydride. The reaction was stirred at room temperature under nitrogen for 17 hr, then 20 ml 0.5 M HCl was added and the mixture was extracted with 2×40 ml diethyl ether. The ether layer was washed with 30 ml saturated NaCl solution and dried (Na2SO4), and the solvent was removed on the rotary evaporator. The product was purified by radial chromatography on a 2 mm silica plate eluting with 50 ml 100% hexane and 100 ml 90% hexane/ether to give 0.27 g (97% yield) of 2-(2-mercapto-2-methylpropylamino)-1-[2-(4-pentenylthio)-2-methylpropylamino]-benzene as an oil.

Workup

  1. extractionthe mixture was extracted with 2×40 ml diethyl ether
  2. washThe ether layer was washed with 30 ml saturated NaCl solution
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed on the rotary evaporator
  5. customThe product was purified by radial chromatography on a 2 mm silica plate
  6. washeluting with 50 ml 100% hexane and 100 ml 90% hexane/ether

Sources & evidence

ORD record
ord-fc1d405ba6f94c198017f8bedd5e3ef4
Source dataset
uspto-grants-1992_01
Patent number
US05080884

Reaction notes

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