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4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-{1-[2-(4-cyanophenoxy)ethyl]ureido}ethyl ester

HRID 899124
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HRID 899124 반응식
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][CH2:9][N:10]([CH2:14][CH2:15][OH:16])[C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1)#[N:2].C([Li])CCC.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][N:10]([CH2:14][CH2:15][O:16][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=2)(=[O:32])=[O:31])[C:11]([NH2:13])=[O:12])=[CH:17][CH:18]=1)#[N:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 69067579N-[2-(4-Cyanophenoxy)ethyl]-N-(2-hydroxyethyl)ureaHCID 178418339Butyllithium

생성물 1

HCID 86616242Toluene-4-sulfonic acid 2-{1-[2-(4-cyanophenoxy)ethyl]ureido}ethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of intermediate 1-[2-(4-cyanophenoxy)ethyl]-1-(2-hydroxy-ethyl)urea (4.7 g, 0.0188 mol; see step (i) above) in dry THF (150 mL) was added n-butyllithium (18.89 mL, 1.1 M) at −78° C. The reaction mixture was stirred at −78° C. for 1 h, after which a solution of freshly crystallised p-toluenesulfonyl chloride (4.3 g, 0.023 mol) in THF (50 mL) was added dropwise. The reaction mixture was then stirred at −78° C. for a further 30 min, before being warmed to −30° C., and stirred for 2 h more. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, concentrated and the residue was recrystallised in ethyl acetate/hexane to yield the title compound as an off-white solid. Yield: 3.5 g.

후처리

  1. stirringThe reaction mixture was then stirred at −78° C. for a further 30 min
  2. temperaturebefore being warmed to −30° C.
  3. stirringstirred for 2 h more
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customthe residue was recrystallised in ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-e1d92b6af75444748c6306b7e641ee48
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07354917B2

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