Benzoyl chloride → HCID 71468850, Verbindung

HRID 1401089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1401089
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]([N:14]([CH:24]([CH3:26])[CH3:25])[NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])=[CH:2]1.CCN(C(C)C)C(C)C.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOC(C)=O>[C:36]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]([N:14]([CH:24]([CH3:26])[CH3:25])[NH:15][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:13])=[CH:2]1)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Komponenten

7

Edukt 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 71468594HCID 71468594, Verbindung

Produkt 1

HCID 71468850HCID 71468850, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a round bottom flask, (E)-N′-(3-(1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide (50 mg, 0.14 mmol, 1.0 equivalent), and DMAP (cat, 4.0 mg, 0.14 equivalent) were introduced and dissolved in CH2Cl2, after which DIPEA (0.04 ml, 0.20 mmol, 1.5 equivalent) was introduced. After introducing benzoyl chloride (0.02 ml, 0.17 mmol, 1.2 equivalent) at 0° C. and stirring at room temperature for 24 hr, the reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (n-hexane:EtOAc:=1:1) and dried so that solid form of (E)-N′-(3-(1-benzoyl-1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide was obtained. (48.0 mg, 77%).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated through silica gel chromatography (n-hexane:EtOAc:=1:1)
  6. dry with materialdried so that solid form of (E)-N′-(3-(1-benzoyl-1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide
  7. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-33cde847c0d3457aaf01ecba9b666ca7
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906952B2

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