4-Bromobenzaldehyde → HCID 86756425, compound

HRID 635843Notes

Reaction equation

HRID 635843 reaction equation
C[C:2]1[N:3]2[C:9]([C:10](=[O:12])[CH3:11])=[CH:8][N:7]=[C:4]2[S:5][CH:6]=1.[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.C[O-].[Na+]>C1COCC1>[Br:13][C:14]1[CH:21]=[CH:20][C:17](/[CH:18]=[CH:11]/[C:10]([C:9]2[N:3]3[C:4]([S:5][CH:6]=[CH:2]3)=[N:7][CH:8]=2)=[O:12])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 707414-BromobenzaldehydeHCID 10942334Sodium MethoxideHCID 21256504HCID 21256504, compound

Product 1

HCID 86756425HCID 86756425, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(3-methylimidazo[2,1-b]thiazol-5-yl)ethanone (Formula B-1) (1.8 g) in THF (25 mL) was treated with 4-bromobenzaldehyde (3.05 mL) and sodium methoxide (0.27 g) at 25°. Within 5 minutes a heavy precipitate formed and additional THF (65 mL) was added to maintain fluididy. After 20 minutes the reaction was concentrated in vacuo and the concentrate was diluted with water and precipitated 2-(4-Bromophenyl)-E-ethenylimidazo[2,1-b]thiazole-5-yl methanone (Formula B-9) (2.9 g) was filtered. The precipitate was recrystallized from ethanol to yield pure 2-(4-Bromophenyl)-E-ethenylimidazo[2,1-b]thiazol-5-yl methanone (Formula B-9) (2.8 g, 81%), m.p. 213-215°.

Workup

  1. customWithin 5 minutes a heavy precipitate formed
  2. temperatureto maintain fluididy
  3. concentrationAfter 20 minutes the reaction was concentrated in vacuo
  4. additionthe concentrate was diluted with water
  5. customprecipitated 2-(4-Bromophenyl)-E-ethenylimidazo[2,1-b]thiazole-5-yl methanone (Formula B-9) (2.9 g)
  6. filtrationwas filtered
  7. customThe precipitate was recrystallized from ethanol

Sources & evidence

ORD record
ord-e9057a661ba247589992568e205bd388
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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