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

HRID 500356

반응식

HRID 500356 반응식
[C:1]([NH:5][S:6]([CH2:9][CH2:10][CH2:11]Cl)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC>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]

참가 물질

4

반응물 2

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

생성물 1

HCID 22499301N-tert-Butylcyclopropanesulfonamide수율 56.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at −78° C. The reation mixture was allowed to warm up to room temperature over period of 1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC 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 (b, 1H).

후처리

  1. customThe volatiles were removed in vacuo
  2. customThe residue was partitioned between EtOAC 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

출처 및 근거

ORD 기록
ord-b767f5530c2b4c62aa5b1bdaef7c4b28
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772183B2

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