Triethylamine → N-ethoxalylindoline

HRID 52459

반응식

HRID 52459 반응식
[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]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 10328IndolineHCID 20884Ethoxalyl chloride

생성물 1

HCID 1581489N-ethoxalylindoline수율 108.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7502193e0e7e4d59a65bd231224295fd
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616586

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