Water → HCID 11502325, Verbindung

HRID 505927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505927
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[N+:18]([O-:20])=[O:19])[NH:11][C:10]=2[CH3:21])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[N+:18]([O-:20])=[O:19])[N:11]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:10]=2[CH3:21])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 116021623-(4-Chlorophenylsulfanyl)-2-methyl-4-nitro-1H-indole

Produkt 1

HCID 11502325HCID 11502325, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel3×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

3-(4-Chlorophenylsulfanyl)-2-methyl-4-nitro-1H-indole (3.76 kg, 11.8 mol) and potassium carbonate (1.80 kg, 13.0 mol) were suspended in acetonitrile (32.7 kg). Water (0.53 kg) and a solution of ethyl bromoacetate (2.17 kg, 13.0 mol) in acetonitrile (5.75 kg) were added followed by an acetonitrile line rinse (2.97 kg). The mixture was heated at 50° C. for 6 hours then allowed to cool to 20° C. and held at this temperature overnight. Water (35.4 kg) was added to the reaction mixture and stirring continued for 30 minutes at 15° C. The solid product was collected by filtration, washed with acetonitrile (2.95 kg) then dried in a vacuum oven at 40° C. to afford [3-(4-chlorophenylsulfanyl)-2-methyl-4-nitro-1H-indol-1-yl]acetic acid, ethyl ester as a bright yellow solid, 4.33 kg (91%).

Aufarbeitung

  1. washrinse (2.97 kg)
  2. temperatureto cool to 20° C.
  3. customheld at this temperature overnight
  4. additionWater (35.4 kg) was added to the reaction mixture
  5. filtrationThe solid product was collected by filtration
  6. washwashed with acetonitrile (2.95 kg)
  7. customthen dried in a vacuum oven at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-2ec6444dbbc143fd9fe36e39eb337bd2
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781598B2

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