N-tert-butyl-3-chloropropane-1-sulfonamide → N-tert-Butylcyclopropanesulfonamide

HRID 734240Notes

Reaction equation

HRID 734240 reaction equation
[C:1]([NH:5][S:6]([CH2:9][CH2:10][CH2:11]Cl)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC>C1COCC1>[C:1]([NH:5][S:6]([CH:9]1[CH2:11][CH2:10]1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11701296N-tert-butyl-3-chloropropane-1-sulfonamideHCID 178418339Butyllithium

Product 1

HCID 22499301N-tert-ButylcyclopropanesulfonamideYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-butyllithium (2.5M in hexane, 8.0 mL, 20.0 mmol) at −78° C. The reaction mixture was allowed to warm up to room temperature over period of 1 hour. The volatiles were removed in vacuo. The residue was partitioned between ethyl acetate and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%). 1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (m, 1H), 4.19 (br, 1H).

Workup

  1. customThe volatiles were removed in vacuo
  2. customThe residue was partitioned between ethyl acetate and water (200 mL, 200 mL)
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-887453cf046844e4a6139a0699047e34
Source dataset
uspto-grants-2009_09
Patent number
US07592336B2

Reaction notes

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