4-Toluenesulfonyl chloride → HCID 11482250, compound

HRID 227285Notes

Reaction equation

HRID 227285 reaction equation
[CH3:1][C:2]([NH2:7])([CH:4]([CH3:6])[CH3:5])[CH3:3].[S:8](Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9]>N1C=CC=CC=1>[S:8]([NH:7][C:2]([CH3:3])([CH:4]([CH3:6])[CH3:5])[CH3:1])([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 2073632,3-dimethylbutan-2-amine

Product 1

HCID 11482250HCID 11482250, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 1.2 g (0.012 mole) 2,3-dimethyl-2-butylamine in 20 mL pyridine, a solution of 1.9 g (0.010 mole) tosylchloride in 20 mL pyridine was added dropwise in a glacial water bath, stirred for 3 hours in that bath and 1 hour at room temperature, then heated for 2 hours in a bath at temperature of 95-100° C. The solvent was distilled off in vacuum. Toluene was added to the residue, then distilled off the solvent in vacuum. The residue was dissolved in water and extracted with toluene (×4). The toluene extract was washed with water once, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled off the solvent. The residue was recrystallized from isopropanol to give a colorless columnar crystal 1.1 g, mp 80-89° C., recrystallized from isopropanol once again to give a white crystal 0.8 g, mp 88-89° C. Elemental analysis for C13H21NO2S (%): Calculated C, 61.14; H, 8.29; N, 5.48. Found C, 61.11;, H, 8.37;, N, 5.55. 1H-NMR(CDCl3; ppm) 0.91(d, J=6.8 Hz, 6H, 2CH3), 1.17(s, 6H, 2CH3), 1.82(M, 1H, CH), 2.47(s, 3H, CH3), 7.32(d,J=8.0, 2H,2Ar—H), 7.82(d, J=8.0, 2H, 2Ar—H′). MS(M/z) 255 (M+), 172(B).

Workup

  1. temperatureheated for 2 hours in a bath at temperature of 95-100° C
  2. distillationThe solvent was distilled off in vacuum
  3. additionToluene was added to the residue
  4. distillationdistilled off the solvent in vacuum
  5. dissolutionThe residue was dissolved in water
  6. extractionextracted with toluene (×4)
  7. extractionThe toluene extract
  8. washwas washed with water once
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. distillationThe filtrate was distilled off the solvent
  12. customThe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-d29a557824f449f088e3a11fadf98f1b
Source dataset
uspto-grants-2009_07
Patent number
US07560473B2

Reaction notes

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