Hydrochloric Acid → 4-n-Propylbenzene t-butylsulfonamide

HRID 36110Notes

Reaction equation

HRID 36110 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:13])=[O:12])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[Li]CCCC.B(OC(C)C)(OC(C)C)OC(C)C.Cl>C1COCC1>[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3].[C:14]([S:11]([NH2:10])(=[O:13])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 194258794-n-Propylphenyl-t-butylsulfonamideHCID 178418339Butyllithium

Product 1

HCID 194258774-n-Propylbenzene t-butylsulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-n-propylphenyl-t-butylsulfonamide (2.85 g, 11.2 mmoL) in anhydrous THF (20 mL) cooled to -40° C. under N2 was added 2.5M n-BuLi solution (11.2 mL, 2.5 equiv). The mixture was warmed to rt and stirred for 2 h. To the mixture, containing the bright red dianion at 0° C., was added B(OiPr)3 (3.9 mL, 1.5 equiv). The next day 2N HCl (3 mL) was added and the mixture was stirred for 1 h. The solvent was removed under reduced pressure and the residue was extracted with EtOAc. The organic was washed with 2N HCl, H2O and brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo to afford the titled compound. Rf=0.5 (1:1 EtOAc/Hex). The crude material was used in subsequent steps without further purification.

Workup

  1. additionTo the mixture, containing the bright red dianion at 0° C.
  2. stirringthe mixture was stirred for 1 h
  3. customThe solvent was removed under reduced pressure
  4. extractionthe residue was extracted with EtOAc
  5. washThe organic was washed with 2N HCl, H2O and brine
  6. dry with materialThe organic was dried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c499ed1d523643029c3e0d4e817a16f2
Source dataset
uspto-grants-1995_05
Patent number
US05412097

Reaction notes

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