Triethylamine → N-ethoxalylindoline

HRID 52459

反応式

HRID 52459 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:17](Cl)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>ClCCl.[Cl-].[Na+].O>[C:17]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:23]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 10328IndolineHCID 20884Ethoxalyl chloride

生成物 1

HCID 1581489N-ethoxalylindoline収率 108.6%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

To a solution of indoline (2.0 g, 16.8 mmol) and triethylamine (5 mL) in dichloromethane (30 mL) was added slowly ethyl chlorooxalate (2.3 mL, 20.1 mmol) at 0° C. The mixture was stirred for 10 min at 0° C. and then for 1 h at room temperature. Brine was added and organic layer was separated. The organic layer was washed with diluted aqueous hydrochloric acid and successively brine, dried over magnesium sulfate, and concentrated to give 4.0 g of N-ethoxalylindoline (100%): 1H NMR (270 MHz, CDCl3) δ8.18 (dd, 1H, J=8, 1 Hz), 7.22 (m, 2H), 7.10 (dd, 1H, J=8, 1 Hz), 4.38 (q, 2H, J=7 Hz), 4.22 (t, 2H, J=8 Hz), 3.20 (t, 2H, J=8 Hz), 1.40 (t, 3H, J=7 Hz).

後処理

  1. waitfor 1 h at room temperature
  2. customorganic layer was separated
  3. washThe organic layer was washed with diluted aqueous hydrochloric acid and successively brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-7502193e0e7e4d59a65bd231224295fd
出典データセット
uspto-grants-1997_04
特許番号
US05616586

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