Tert-Butylamine → HCID 11993908, compound

HRID 1644835Notes

Reaction equation

HRID 1644835 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[CH2:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:7]([CH3:9])[CH3:8].[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17]>C1(C)C=CC=CC=1>[C:16]([NH:20][S:2]([C:13]1[CH:14]=[CH:15][C:10]([CH2:6][CH:7]([CH3:9])[CH3:8])=[CH:11][CH:12]=1)(=[O:5])=[O:3])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 10870IsobutylbenzeneHCID 24638Chlorosulfonic acid

Product 1

HCID 11993908HCID 11993908, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

Chlorosulfonic acid (28.6 mL, 0.43 mol) was added dropwise to stirred iso-butylbenzene (11.14 g, 0.083 mol) at 0° C. The reaction mixture was then heated to 40° C. for 0.5 h, poured into ice-water (150 mL) and extracted with ethyl acetate (400 mL). The organic phase was washed with water and brine and dried over MgSO4. The solvent was removed in vacuo and the residue was dissolved in CHCl3 (50 mL). To this stirred solution, tert-butylamine (43.7 mL, 0.416 mol) was added dropwise. The reaction was heated to reflux for 10 min and then cooled to room temperature. The reaction mixture was then diluted with toluene (200 mL) and washed with water and brine. The organic phase was dried over MgSO4 and the solvent was removed in vacuo. Purification using column chromatography with hexane:acetone (4:1) as eluent yielded the sub-title compound as a white solid (12.0 mg, 0.045 mol) in 54% yield.

Workup

  1. extractionextracted with ethyl acetate (400 mL)
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in CHCl3 (50 mL)
  6. temperatureThe reaction was heated
  7. temperatureto reflux for 10 min
  8. temperaturecooled to room temperature
  9. washwashed with water and brine
  10. dry with materialThe organic phase was dried over MgSO4
  11. customthe solvent was removed in vacuo
  12. customPurification

Sources & evidence

ORD record
ord-8e0c1d7f811f4538902d97493dd37d42
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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