Sodium Hydroxide → HCID 10293154, Verbindung

HRID 913185

Reaktionsgleichung

Reaktionsgleichung von HRID 913185
[N:1]1([CH2:10][C:11]2[O:15][N:14]=[C:13]([CH3:16])[CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:17](Cl)(=[O:21])[C:18](Cl)=[O:19].[CH3:23][C:24]1[CH:28]=[C:27]([NH2:29])[S:26][N:25]=1.[OH-].[Na+]>C(OCC)C.O1CCCC1.C(N(CC)CC)C>[CH3:23][C:24]1[CH:28]=[C:27]([NH:29][C:17](=[O:21])[C:18]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:1]([CH2:10][C:11]3[O:15][N:14]=[C:13]([CH3:16])[CH:12]=3)[CH:2]=2)=[O:19])[S:26][N:25]=1

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 323073-Methylisothiazol-5-amineHCID 65578Oxalyl chlorideHCID 11275877HCID 11275877, Verbindung

Produkt 1

HCID 10293154HCID 10293154, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 5-(1H-1-indolylmethyl)-3-methylisoxazole (212 mg, 1.0 mmol) in 10 mL diethyl ether was added to oxalyl chloride (254 mg, 2.0 mmol) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 3 hours and then the reaction solvent was evaporated. The residue was dissolved in 5 mL tetrahydrofuran and then the 3-methyl-5-isothiazolamine (114 mg, 1.0 mmol) and triethylamine (1 mL) in 10 mL tetrahydrofuran was added dropwise. The mixture was stirred for 10 hours and then 1 N NaOH (4 mL) was added to the reaction flask dropwise. The mixture was extracted three times with a total of 60 mL of tetrahydrofuran, the organic phase was dried using anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuum. The residue was crystallized from methanol. Yield: 0.27 g, 71%.

Aufarbeitung

  1. customthe reaction solvent was evaporated
  2. dissolutionThe residue was dissolved in 5 mL tetrahydrofuran
  3. stirringThe mixture was stirred for 10 hours
  4. extractionThe mixture was extracted three times with a total of 60 mL of tetrahydrofuran
  5. customthe organic phase was dried
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuum
  8. customThe residue was crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-90f023475c684d8ba878bdf3b848dffe
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026271B2

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