2-(5-Nitro-2-pyridinylthio)ethyl-3-chlorobenzoate → 2-[(5-Nitro-2-pyridinyl)sulfinyl]ethyl-3-chlorobenzoate

HRID 731769노트

반응식

HRID 731769 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][CH2:12][O:13][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].ClC1C=CC=C(C(O[O-])=[O:31])C=1>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH2:11][CH2:12][O:13][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[O:31])=[N:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

4

반응물 2

HCID 116242282-(5-Nitro-2-pyridinylthio)ethyl-3-chlorobenzoate2회HCID 14904487m-Chloroperbenzoate

생성물 1

HCID 115304832-[(5-Nitro-2-pyridinyl)sulfinyl]ethyl-3-chlorobenzoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 2-(5-nitro-2-pyridinylthio)ethyl-3-chlorobenzoate, (5) [20 mg, 0.059 mmol; prepared according to the method outlined in Scheme 2; 1H NMR (CDCl3): δ 9.22 (d, J=1.8 Hz, 1H), 8.24 (dd, J=2.4 and 9.0 Hz, 1H), 7.95-7.91 (m, 1H), 7.90 (t, J=0.9 Hz, 1H), 7.56-7.51 (m, 1H), 7.39 (d, J=8.1 Hz, 1H), 7.34 (d, J=8.1 Hz, 1H), 4.61 (t, J=6.6 Hz, 2H), 3.68 (t, J=6.6 Hz, 2H)] and m-chloroperbenzoate (m-CPBA) 50%, 21 mg, 0.060 mmol) was stirred at room temperature for 1.25 h. The reaction mixture was then diluted with dichloromethane and washed with saturated aqueous solution of NaHCO3 and then dried over anhydrous MgSO4. The crude product was purified by silica gel chromatography to give 2-[(5-nitro-2-pyridinyl)sulfinyl]ethyl-3-chlorobenzoate (6). LCMS: purity: 99%; MS (m/e): 355 (MH+).

후처리

  1. customprepared
  2. washwashed with saturated aqueous solution of NaHCO3
  3. dry with materialdried over anhydrous MgSO4
  4. customThe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-7279e71db49340c7a70aa4f101ea9ab4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585883B2

반응 노트

불러오는 중…