Diethyl Ether → 4,7-dichloro-1-pentyl-1H-indole-2,3-dione

HRID 645065노트

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HRID 645065 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]2[C:5]=1[C:6](=[O:15])[C:7](=[O:14])[NH:8]2.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(OCC)C>CN(C)C=O>[Cl:3][C:4]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]2[C:5]=1[C:6](=[O:15])[C:7](=[O:14])[N:8]2[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 27347934,7-Dichloroisatin

생성물 1

HCID 666426684,7-dichloro-1-pentyl-1H-indole-2,3-dione수율 98%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a mixture of sodium hydride (0.17 g, 6.94 mmol, 60% dispersion in mineral oil) in anhydrous N,N-dimethylformamide (5.00 mL) was added a solution of 4,7-dichloro-1H-indole-2,3-dione (1.00 g, 4.60 mmol) in N,N-dimethylformamide (5.00 mL) at 0° C. The brown reaction mixture was stirred for 0.5 h followed by the addition of a solution of 1-bromopentane (0.84 g, 5.55 mmol) in anhydrous N,N-dimethylformamide (5.00 mL). The reaction mixture was stirred at ambient temperature for 16 h and poured into wet ethyl ether (30.0 mL). After the organic layer was separated, it was washed with water (2×20.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The gummy residue was dried under vacuum and the solid was triturated with ether to give the title compound (0.98 g, 98%): MS (ES+) m/z 286.2 (M+1).

후처리

  1. stirringThe reaction mixture was stirred at ambient temperature for 16 h
  2. customAfter the organic layer was separated
  3. washit was washed with water (2×20.0 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness
  7. customThe gummy residue was dried under vacuum
  8. customthe solid was triturated with ether

출처 및 근거

ORD 기록
ord-646f4dbbbfa44212a19e22887f8e6880
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700641B2

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