Acetic Acid → T 691

HRID 1494703Notes

Reaction equation

HRID 1494703 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)[C:15]#[CH:16].C(O)(=O)C.C([BH3-])#N.[Na+]>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][CH2:19][C:18]([S:17][CH2:14][C:15]#[CH:16])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 99893642-(2-Propynylthio)-2-methylpropanalHCID 100129272-Amino-1-(2-mercapto-2-methylpropylamino)benzene

Product 1

HCID 195818T 691Yield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
21 °C

Procedure

2-Amino-1-(2-mercapto-2-methylpropylamino)benzene (5.59 g, 2.85×10-2 mol) and 2-(2-propynylthio)-2-methylpropanal 6.07 g, 4.28×10-2 mol, 150 M %) were mixed, then 125 ml methanol and 5.27 ml (5.7×10-2 mol, 200 M %) acetic acid were added and solids were allowed to dissolve. Sodium cyanoborohydride (5.39 g, 8.56×10-2 mol, 300 M %) was added to the reaction solution in three equal portions. The reaction was stirred at 21° C. for 17 hr, then quenched with 100 ml 0.5M HCl, stirred for 15 min, and then extracted with 2×150 ml ether. The ether layers were combined, washed with 60 ml saturated NaCl solution and dried over Na2SO4. The solvent was removed on the rotary evaporator and the residue was purified by filtration through flash silica in a 600 ml sintered glass funnel 3/4 full of silica, eluting with 500 ml portions of 2 × hexane and 2× 90% hexane/ether to produce 6.88 g (75% yield) 2-(2-mercapto-2-methyl-propylamino)-1-[2-(2-propynylthio)-2methylpropylamino]-benzene.

Workup

  1. dissolutionto dissolve
  2. customquenched with 100 ml 0.5M HCl
  3. stirringstirred for 15 min
  4. extractionextracted with 2×150 ml ether
  5. washwashed with 60 ml saturated NaCl solution
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed on the rotary evaporator
  8. filtrationthe residue was purified by filtration through flash silica in a 600 ml sintered glass funnel 3/4 full of silica
  9. washeluting with 500 ml portions of 2 × hexane and 2× 90% hexane/ether

Sources & evidence

ORD record
ord-ec94d2e08c944fe9be857b852d19bd30
Source dataset
uspto-grants-1991_06
Patent number
US05026913

Reaction notes

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