Chloroacetonitrile → HCID 671500, Verbindung

HRID 2173665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173665
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([C:10]#[N:11])[C:5](=[S:9])[NH:6][C:7]=1[CH3:8].[OH-].[K+].Cl[CH2:16][C:17]#[N:18]>CN(C=O)C>[NH2:11][C:10]1[C:4]2[C:5](=[N:6][C:7]([CH3:8])=[C:2]([Cl:1])[C:3]=2[CH3:12])[S:9][C:16]=1[C:17]#[N:18]

Komponenten

5

Edukt 3

HCID 7856ChloroacetonitrileHCID 14797Potassium Hydroxide2×HCID 115646615-chloro-4,6-dimethyl-2-sulfanylidene-1H-pyridine-3-carbonitrile

Produkt 1

HCID 671500HCID 671500, VerbindungAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The 5-chloro-4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile (300 mg, 1.51 mmol) was stirred in the DMF (3.0 mL). An aqueous solution of 10% KOH (0.85 mL, 1.51 mmol) was added, followed by chloroacetonitrile (0.095 mL, 1.51 mmol). The reaction was stirred at RT for 15 minutes, LC/MS indicates initial thio-alkylation is complete. A second equivalent of 10% KOH (0.85 mL, 1.51 mmol) was added and the resulting slurry was warmed to 50° C. and stirred about 30 min. LC/MS indicates reaction is done. The slurry was cooled to RT, then poured into 50 g of crushed ice and allowed to warm until the ice melted. The cold slurry was poured through filter paper, washing the solid with cold water. The solid was collected and dried in a vacuum oven at 60° C. to give 310 mg (86%) of the pure product as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 6.56 (s, 1H), 2.80 (s, 3H), 2.62 (s, 3H). LC/MS: RT=0.73 min., m/z=238.0 [M+H]+.

Aufarbeitung

  1. temperaturethe resulting slurry was warmed to 50° C.
  2. stirringstirred about 30 min
  3. customreaction
  4. temperatureThe slurry was cooled to RT
  5. additionThe cold slurry was poured
  6. filtrationthrough filter paper
  7. washwashing the solid with cold water
  8. customThe solid was collected
  9. customdried in a vacuum oven at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-3064fdf81d264db48a9c6909de41f20d
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056876B2

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