Chloroacetyl chloride → 1-(2-Chloroacetyl)-3,3-dimethylindoline-6-carbonitrile

HRID 1475409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1475409
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[NH:4][CH2:3]1.C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)Cl.O>[Cl:21][CH2:22][C:23]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=2)[C:2]([CH3:13])([CH3:1])[CH2:3]1)=[O:24]

Komponenten

6

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 107023412,3-dihydro-3,3-dimethyl-1H-indole-6-carbonitrile

Produkt 1

HCID 867240061-(2-Chloroacetyl)-3,3-dimethylindoline-6-carbonitrileAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3,3-dimethylindoline-6-carbonitrile (0.35 g, 2.0 mmol) and triethylamine (0.56 mL, 4.0 mmol) in DCM (10 mL) at 0° C. was added chloroacetyl chloride (0.16 mL, 2.0 mmol) dropwise. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was then diluted with water. The organic phase was then separated, dried over magnesium sulfate and concentrated to give the title compound (0.39 g). 1H NMR (CDCl3): 8.47 (s, 1H), 7.40 (d, 1H), 7.24 (d, 1H), 4.14 (s, 2H), 3.94 (s, 2H), 1.42 (s, 6H).

Aufarbeitung

  1. customThe organic phase was then separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d5f0e16947f44766a9f737d75b2fa2f5
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018214B2

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