Potassium Carbonate → 1-Methyl-5-[[7-(3-methyl-5-isoxazolyl)heptyl]thio]-1H-tetrazole

HRID 729101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729101
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]Br)[O:4][N:3]=1.[CH3:15][N:16]1[C:20]([SH:21])=[N:19][N:18]=[N:17]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:15][N:16]1[C:20]([S:21][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:5]2[O:4][N:3]=[C:2]([CH3:1])[CH:6]=2)=[N:19][N:18]=[N:17]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 133169675-(7-Bromoheptyl)-3-methylisoxazoleHCID 178482017HCID 178482017, Verbindung

Produkt 1

HCID 540426221-Methyl-5-[[7-(3-methyl-5-isoxazolyl)heptyl]thio]-1H-tetrazoleAusbeute 101,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

7-(3-methylisoxazole-5-yl)heptylbromide (520 mg, 0.002 mol) was added to a mixture of 1-methyltetrazole thiol (232 mg, 0.002 mol) and potassium carbonate (276 mg, 0.002 mol) in anhydrous acetone (20 ml) while stirring.The mixture was heated under reflux for 3 hours. After cooling, the mixturewas filtered and the filtrate was concentrated under reduced pressure. The residual oil as dissolved in dichloromethane (50 ml), washed with water (50 ml×2), with 5% aqueous solution of potassium hydroxide (10 ml) and again with water (50 ml×2). The organic layer was dried over sodium sulfate. Removal of the solvent gave a yellow oil (600 mg) which was purified by elution from a silica gel column using methanol-dichloromethane (5:95) as an eluant to give 80% (472 mg) of a colorless oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe mixturewas filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residual oil as dissolved in dichloromethane (50 ml)
  7. washwashed with water (50 ml×2), with 5% aqueous solution of potassium hydroxide (10 ml) and again with water (50 ml×2)
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-eca0f73b5545408dbcabcb8f90060d8e
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05051515

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