Methyl bromoacetate → HCID 15027716, Verbindung

HRID 345961

Reaktionsgleichung

Reaktionsgleichung von HRID 345961
CC(C)([O-])C.[K+].[C:7]([CH2:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14]C)=O)#[N:8].[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]=[C:28]=[S:29].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33]>O1CCCC1.O>[NH2:8][C:7]1[C:9]2[C:10]3[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=3[C:12](=[O:14])[N:27]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[Cl:20])[C:28]=2[S:29][C:31]=1[C:32]([O:34][CH3:35])=[O:33]

Komponenten

7

Edukt 4

HCID 60984Methyl bromoacetateHCID 1231711-Chloro-2-isothiocyanatobenzeneHCID 588805Methyl 2-(cyanomethyl)benzoateHCID 23665647Potassium tert-butoxide2×

Produkt 1

HCID 15027716HCID 15027716, VerbindungAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1.85 g of potassium t-butoxide in 32.3 ml of a dry tetrahydrofuran was added 2.83 g of methyl 2-cyanomethylbenzoate with stirring under an ice-cooling in a stream of nitrogen, and then to the mixture was added 3.02 g of 2-chlorophenyl isothiocyanate for 10 minutes. The mixture was stirred under an ice-cooling for 10 minutes. To the reaction mixture was added 2.72 g of methyl bromoacetate for 10 minutes, and the mixture was stirred for 80 minutes at room temperature. The reaction mixture was cooled under an ice-bath, and 363 mg of potassium t-butoxide was added to the cold mixture. The mixture was stirred for 1 hour under an ice-cooling. To the reaction mixture was added 70 ml of water for 2 minutes, and the mixture was stirred for 15 minutes. Precipitates were collected by a filtration, and successively washed with water, methanol and hexane, and dried under reduced pressure to obtain 4.87 g of the desired product as white colorless crystals.

Aufarbeitung

  1. temperaturecooling in a stream of nitrogen
  2. stirringThe mixture was stirred under an ice-
  3. temperaturecooling for 10 minutes
  4. stirringthe mixture was stirred for 80 minutes at room temperature
  5. temperatureThe reaction mixture was cooled under an ice-bath
  6. stirringThe mixture was stirred for 1 hour under an ice-
  7. temperaturecooling
  8. stirringthe mixture was stirred for 15 minutes
  9. customPrecipitates
  10. filtrationwere collected by a filtration
  11. washsuccessively washed with water, methanol and hexane
  12. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1070a67d6d994296bc03ffd2ef84c22d
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05059692

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