Benzaldehyde → 2,3-Dimethyl-(2-phenyl-E-ethenyl)imidazo[2,1-b]thiazol-5-yl methanone

HRID 635849

Reaction equation

HRID 635849 reaction equation
[CH3:1][C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([C:10](=[O:12])[CH3:11])[N:4]2[C:3]=1[CH3:13].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C[O-].[Na+]>C1COCC1>[CH3:1][C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([C:10](/[CH:11]=[CH:14]/[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[N:4]2[C:3]=1[CH3:13]

Participants

5

Reactant 3

HCID 240Benzaldehyde2×HCID 10942334Sodium MethoxideHCID 212564452,3-Dimethylimidazo[2,1-b]thiazol-5-yl ethanone2×

Product 1

HCID 212565022,3-Dimethyl-(2-phenyl-E-ethenyl)imidazo[2,1-b]thiazol-5-yl methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(2,3-dimethylimidazo[2,1-b]thiazole-5-yl ethanone (See procedures from Preparation 6) (Formula D-1) (0.87 g) in THF (25 mL) was treated with benzaldehyde (0.52 mL) and sodium methoxide (0.11 g). After 18 hours trace 1-(2,3-dimethylimidazo[2,1-b]thiazol-5-yl ethanone remained and additional benzaldehyde (0.2 mL) was added. After an additional 2.5 hours the reaction was diluted with ice water and precipitated 2,3-Dimethyl-(2-phenyl-E-ethenyl)imidazo[2,1-b]thiazol-5-yl methanone (FIG. D-2) (1.03 g) was filtered. Crystallization from isopropanol solution gave pure 2,3-Dimethyl-(2-phenyl-E-ethenyl)imidazo[2,1-b]thiazol-5-yl methanone (FIG. D-2), m.p. 189-190°.

Workup

  1. customprecipitated 2,3-Dimethyl-(2-phenyl-E-ethenyl)imidazo[2,1-b]thiazol-5-yl methanone (FIG. D-2) (1.03 g)
  2. filtrationwas filtered
  3. customCrystallization from isopropanol solution

Sources & evidence

ORD record
ord-efe77d216995480d8840f4818aead038
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Linked notes

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