Dimethylformamide → 4-methoxy-N7,N7-dimethyl-benzothiazole-2,7-diamine

HRID 51868

Reaktionsgleichung

Reaktionsgleichung von HRID 51868
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2C(N)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].IC.[CH3:22][N:23]([CH:25]=O)[CH3:24]>>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:25]([N:23]([CH3:22])[CH3:24])=[CH:5][CH:4]=1

Komponenten

5

Edukt 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 227369774-Methoxy-1,3-benzothiazole-2,7-diamine

Produkt 1

HCID 227370024-methoxy-N7,N7-dimethyl-benzothiazole-2,7-diamineAusbeute 26 %

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirred solution of 2.00 g (1.02 mmol) 4-methoxy-benzothiazole-2,7-diamine in 30 ml DMF at room temperature was added 4.25 g (3.07 mmol) potassium carbonate and the mixture heated to 50° C. A solution of 0.64 ml (1.02 mmol) iodomethane in 10 ml DMF was then added dropwise over 3 h and stirring continued for a further 1 h at 50° C. The mixture was then filtered and the filtrate concentrated in vacuo. Flash chromatography (20/1 dichloromethane/methanol) afforded 600 mg (26%) 4-methoxy-N7,N7-dimethyl-benzothiazole-2,7-diamine as a yellow solid, ES-MS m/e (%): 224 (M+H+, 100); 540 mg (25%) 4-methoxy-N7-methyl-benzothiazole-2,7-diamine as a yellow solid, ES-MS m/e (%): 210 (M+H+, 100) and 340 mg (17%) recovered starting material.

Aufarbeitung

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3e7177a036404a6987b0414536212ffc
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713499B2

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