Dimethylformamide → 5-Methoxy-2-methyl-1H-indole-3-carbonitrile

HRID 889901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889901
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[CH:6]2.[C:13](#[N:15])C.ClS(N=C=O)(=O)=O.CN(C)C=O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[C:13]#[N:15]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 706425-Methoxy-2-methylindoleHCID 70918Chlorosulfonyl isocyanate

Produkt 1

HCID 222500905-Methoxy-2-methyl-1H-indole-3-carbonitrileAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a 0° C. solution of 5-Methoxy-2-methyl-1H-indole (5 g, 31.0 mmol), dry acetonitrile, (90 mL) was slowly added chlorosulfonyl isocyanate (3 mL, 34.1 mmol). The reaction was stirred and allowed to warm to room temperature and stirred for an additional four hours followed by the addition of dimethyl formamide (4.8 mL (62.0 mmol)and then stirred for an additional 1.5 hours at room temperature. The reaction was poured into water and extracted with diethyl ether. The aqueous layer was adjusted to pH 9 with 1M potassium carbonate, and extracted with diethyl ether. The ether layers were combined and dried over magnesium sulfate, filtered and concentrated. Crystallization of the residue from ether and hexane gave 5-methoxy-2-methyl-1H-indole-3-carbonitrile (3.86 g) in 67% yield as a light pink solid. C11H10N2O: GC/MS r.t.=4.06 min., m/z 186; 1H NMR (CDCl3): δ 7.22 (d, 1H, J=8.3 Hz), 7.08 (s, 1H), 6.86 (d, 1H, J=8.3 Hz), 3.86 (s, 3H), 2.60 (s, 3H) ppm.

Aufarbeitung

  1. customTo a 0° C.
  2. stirringstirred for an additional four hours
  3. stirringstirred for an additional 1.5 hours at room temperature
  4. extractionextracted with diethyl ether
  5. extractionextracted with diethyl ether
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customCrystallization of the residue from ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-ef16703b86734a708b928469a1eba742
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995171B2

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