Thionyl Chloride → 2-(2-Chloroethyl)isoindolin-1-one

HRID 50998

反応式

HRID 50998 の反応式
O[CH2:2][CH2:3][N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:13].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[Cl:16][CH2:2][CH2:3][N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:13]

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 2201052-(2-hydroxyethyl)-3H-isoindol-1-one

生成物 1

HCID 27835142-(2-Chloroethyl)isoindolin-1-one収率 92%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
20 °C

実験手順

To a solution of 2-(2-hydroxyethyl)isoindolinone (1.0 g, 5.64 mmol) in toluene (3.5 mL) was added thionyl chloride (1.34 g, 11.3 mmol). The reaction mixture was stirred at 20° C. for 3 h then 4 h at 60° C. The reaction mixture was concentrated in vacuo to remove excess thionyl chloride and toluene. 2-(2-Chloroethyl)isoindolinone (1.01 g, 92%) was obtained by flash chromatography on a silica gel column by elution with EtOAc/Hexanes a white solid. 1H NMR (CDCl3, 300 MHz) δ3.81 (t, 2H, J=5.5 Hz), 3.97 (t, 2H, J=5.9 Hz), 4.59 (s, 2H), 7.44-7.58 (m, 3H), 7.86 (d, 1H, J=6.9 Hz) ppm.

後処理

  1. custom4 h
  2. customat 60° C
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto remove excess thionyl chloride and toluene

出典と根拠

ORDレコード
ord-e0267091dd654bfe9522c6cfa47d094b
出典データセット
uspto-grants-2004_03
特許番号
US06713471B1

関連ノート

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