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

HRID 461835Notes

Reaction equation

HRID 461835 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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%.

Workup

  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°

Sources & evidence

ORD record
ord-e40a365811f14ea0aaef229547e0b3b6
Source dataset
uspto-grants-1977_12
Patent number
US04064260

Reaction notes

Loading…