HCID 21256450, compound → 174209-00-8

HRID 635847Notes

Reaction equation

HRID 635847 reaction equation
[CH3:1][C:2]1[N:3]2[C:9]([CH2:10][OH:11])=[CH:8][N:7]=[C:4]2[S:5][CH:6]=1>CN(C=O)C.C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:1][C:2]1[N:3]2[C:9]([CH:10]=[O:11])=[CH:8][N:7]=[C:4]2[S:5][CH:6]=1

Participants

5

Reactant 1

HCID 21256450HCID 21256450, compound

Product 1

HCID 21256490174209-00-8Yield 22.7%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-Methylimidazo[2,1-b]thiazole-5-methanol (FIG. C-5) (0.9 g) in DMF (10 mL) was diluted with toluene (200 mL), treated with MnO2 (3.0), and azeotropically distilled for 1.5 hours. The suspension was filtered and the filtrate was concentrated to 10 mL. The concentrate was diluted with ice water and the precipitated 3-Methylimidazo[2,1-b]thiazole-5-carboxaldehyde (FIG. C-6) (0.665 g) was filtered. An aliquot (225 mg) was recrystallized from ethyl acetate-hexane to yield pure 3-Methylimidazo[2,1-b]thiazole-5-carboxaldehyde (FIG. C-6) (202 mg), m.p. 163-165°.

Workup

  1. distillationazeotropically distilled for 1.5 hours
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated to 10 mL
  4. additionThe concentrate was diluted with ice water
  5. filtrationthe precipitated 3-Methylimidazo[2,1-b]thiazole-5-carboxaldehyde (FIG. C-6) (0.665 g) was filtered
  6. customAn aliquot (225 mg) was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1cfbedca2f9d430bab25174ce5e20675
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

Loading…