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Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 5,6-Bis(4-methoxyphenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole

HRID 461835
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Reaktionsgleichung

Reaktionsgleichung von HRID 461835
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([SH:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C[O-].[Na+].Cl[CH2:27][CH2:28]OS(C1C=CC(C)=CC=1)(=O)=O>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]3[C:11]([S:22][CH2:27][CH2:28]3)=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1
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Komponenten

5

Edukt 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)2×HCID 10942334Sodium MethoxideHCID 178489021HCID 178489021, Verbindung

Produkt 1

HCID 128749955,6-Bis(4-methoxyphenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a stirred slurry of 3.1 g (0.01 mole) 4,5 bis-(p-methoxyphenyl)-2-mercaptoimidazole [Anschutz and Schwickerath, Ann., 284, 24 (1895)] in 50 ml methanol was added 0.65 g (0.012 mole) of sodium methoxide. To the resulting solution was added 2.6 g (0.011 mole) 2-chloroethyl-p-toluenesulfonate in 10 ml methanol. The mixture was heated at reflux overnight. Another 0.5 g (0.002 mole) of 2-chloroethyl-p-toluenesulfonate was added and refluxing was continued another 2 hours. The mixture was poured into ice water and extracted with methylene chloride three times. The methylene chloride layers were dried and concentrated on a rotary evaporator. The residue was chromatographed on silica gel, eluting with chloroform. The product was obtained by trituration of fractions 4 and 5 with ether to give crystalline material, m.p. 149°-151°. Analysis by IR, NMR and CHN microanalysis indicated the product in a purity of about 85%.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperaturerefluxing
  4. extractionextracted with methylene chloride three times
  5. dry with materialThe methylene chloride layers were dried
  6. concentrationconcentrated on a rotary evaporator
  7. customThe residue was chromatographed on silica gel
  8. washeluting with chloroform
  9. customThe product was obtained by trituration of fractions 4 and 5 with ether
  10. customto give crystalline material, m.p. 149°-151°

Quellen und Nachweise

ORD-Eintrag
ord-e40a365811f14ea0aaef229547e0b3b6
Quelldatensatz
uspto-grants-1977_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04064260

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