Potassium Carbonate → HCID 59591441, Verbindung

HRID 1963000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963000
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]#[N:11].C([O-])([O-])=O.[K+].[K+].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.[Cl:34][C:35]1[CH:36]=[CH:37][C:38]2[S:42][C:41]([CH2:43]Cl)=[N:40][C:39]=2[CH:45]=1>CN(C=O)C.O>[Cl:34][C:35]1[CH:36]=[CH:37][C:38]2[S:42][C:41]([CH2:43][O:8][C:7]3[C:2]([F:1])=[C:3]([C:10]#[N:11])[C:4]([F:9])=[CH:5][CH:6]=3)=[N:40][C:39]=2[CH:45]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 1859152-NaphthylalanineHCID 107988395-Chloro-2-(chloromethyl)-1,3-benzothiazoleHCID 451191012,6-Difluoro-3-hydroxybenzonitrile

Produkt 1

HCID 59591441HCID 59591441, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2,6-difluoro-3-hydroxybenzenecarbonitrile (4.5 g, 29.0 mmol), K2CO3 (6.01 g, 43.5 mmol) and Nal (0.78 g 5.8 mmol) in DMF (75 ml) was stirred at room temperature for 5 minutes. 5-chloro-2-(chloromethyl)-1,3-benzothiazole was then added and the mixture heated at 40° C. for 18 hours, cooled to room temperature and poured into water (450 ml). Buff solid was filtered off and dried (9.46 g). This was the recrystallised from acetonitrile (30 ml) and dried in vacuo at 40° C. to give a beige solid. Yield 79%, mp 145-147° C., HPLC (Gemini C18, 50×4.6 mm): m/z 337 [M+H]+, Rt=4.93 min.

Aufarbeitung

  1. temperaturethe mixture heated at 40° C. for 18 hours
  2. temperaturecooled to room temperature
  3. filtrationBuff solid was filtered off
  4. customdried (9.46 g)
  5. customrecrystallised from acetonitrile (30 ml)
  6. customdried in vacuo at 40° C.
  7. customto give a beige solid

Quellen und Nachweise

ORD-Eintrag
ord-057c172684ac495987a9fc0f6c25c561
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415383B2

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