Pyridine → 2-[(5-Nitro-2-pyridinyl)thio]ethyl 4-chlorobenzoate

HRID 731767ノート

反応式

HRID 731767 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][CH2:12][OH:13])=[N:8][CH:9]=1)([O-:3])=[O:2].[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.N1C=CC=CC=1>ClCCl>[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([O:13][CH2:12][CH2:11][S:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)=[O:20])=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 85014-Chlorobenzoyl chlorideHCID 433853802-[(5-Nitro-2-pyridinyl)thio]ethanol

生成物 1

HCID 114938062-[(5-Nitro-2-pyridinyl)thio]ethyl 4-chlorobenzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A homogeneous mixture of 2-[(5-nitro-2-pyridinyl)thio]ethanol (7) (45 mg, 0.22 mmol), 4-chlorobenzoyl chloride (33 μL, 0.26 mmol) and pyridine (45 μL, 0.56 mmol) in anhydrous dichloromethane (1.5 mL) was stirred at room temperature for 48 h. The reaction mixture was quenched with 1N HCl and the organic phase was washed with saturated aqueous solution of NaHCO3, brine and then dried over anhydrous MgSO4. The crude product was purified by silica gel chromatography to give 2-[(5-nitro-2-pyridinyl)thio]ethyl 4-chlorobenzoate (8). LCMS: purity: 90%; MS (m/e): 340 (M+)

後処理

  1. customThe reaction mixture was quenched with 1N HCl
  2. washthe organic phase was washed with saturated aqueous solution of NaHCO3, brine
  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-9bbe25831e9c45c39f003ee4b950b899
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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