Dimethylformamide → 2-Oxo-2,3-dihydro-benzothiazole-6-carbonitrile

HRID 911572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911572
Br[C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[CH:7][S:8](=O)[C:4]=2[CH:3]=1.[Cu]([C:15]#[N:16])C#N.CN(C=[O:21])C.[C-]#N.[Na+]>O>[O:21]=[C:7]1[NH:6][C:5]2[CH:10]=[CH:11][C:2]([C:15]#[N:16])=[CH:3][C:4]=2[S:8]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 667018736-BromobenzothiazolinoneHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 667072472-Oxo-2,3-dihydro-benzothiazole-6-carbonitrileAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Combine 6-bromobenzothiazolinone (2 g, 8.69 mmol), copper cyanide (1.3 g, 1.48 mmol), anhydrous DMF (5 mL) and heat at reflux for 15 h. Add water (20 mL) and sodium cyanide (1.4 g, 27.7 mmol) at 100° C. Cool the reaction mixture to room temperature and stir for 2 h. Extract the reaction mixture with EtOAc (5×30 mL) at 70° C. Combine the organic layers, wash with water (3×40 mL) and dry over anhydrous Na2SO4. Concentrate in vacuo to obtain the desired intermediate as a yellow solid (2 g, 87%). GC-MS m/z: 176 (M+).

Aufarbeitung

  1. temperatureat reflux for 15 h
  2. customat 100° C
  3. extractionExtract the reaction mixture with EtOAc (5×30 mL) at 70° C
  4. washwash with water (3×40 mL)
  5. dry with materialdry over anhydrous Na2SO4
  6. concentrationConcentrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-35d14f33c1dd40d98cb5565d9c5f4d6f
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022062B2

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