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

HRID 731769ノート

反応式

HRID 731769 の反応式
[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]

参加物

4

反応物 2

HCID 116242282-(5-Nitro-2-pyridinylthio)ethyl-3-chlorobenzoate2 回HCID 14904487m-Chloroperbenzoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-7279e71db49340c7a70aa4f101ea9ab4
出典データセット
uspto-grants-2009_09
特許番号
US07585883B2

反応ノート

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