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

HRID 544824

Reaction equation

HRID 544824 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 warmed to room temperature over a period of 1 hour and concentrated in vacuo. The concentrate was partitioned between ethyl acetate and water (200 mL, 200 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The concentrate was recrystallized from hexane to provide 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. concentrationconcentrated in vacuo
  2. customThe concentrate was partitioned between ethyl acetate and water (200 mL, 200 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe concentrate was recrystallized from hexane

Sources & evidence

ORD record
ord-1a8cf39d74bb4b709ac779d87637a9df
Source dataset
uspto-grants-2011_05
Patent number
US07935670B2

Linked notes

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