HCID 21256500, compound → HCID 21256457, compound

HRID 635864Notes

Reaction equation

HRID 635864 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]3[C:11]([CH2:12][OH:13])=[CH:10][N:9]=[C:7]3[S:8][C:4]=2[CH:3]=1>CN(C=O)C.C1(C)C=CC=CC=1.O=[Mn]=O>[F:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]3[C:11]([CH:12]=[O:13])=[CH:10][N:9]=[C:7]3[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 1

HCID 21256500HCID 21256500, compound

Product 1

HCID 21256457HCID 21256457, compoundYield 89.8%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-Fluoro-imidazo[2,1-b]benzothiazole-3-methanol (Formula L-2) (1.0 g) in DMF (5 mL) was diluted with toluene (200 mL), the warm solution was treated with activated MnO2 (2.34 g) and azeotropically distilled for 4 hours. The cooled suspension ws filtered, the filtrate was concentrated in vacuo and the residue was diluted with ice water. Precipitated 7-Fluoro-imidazo [2,1-b]benzothiazole-3-carboxaldehyde (Formula L-3) was filtered and recrystallized from acetonitrile to yield pure 7-Fluoro-imidazo[2,1-b]benzothiazole-3-carboxaldehyde (Formula L-3) (0.89 g), m.p. 182-183°.

Workup

  1. distillationazeotropically distilled for 4 hours
  2. filtrationThe cooled suspension ws filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionthe residue was diluted with ice water
  5. filtrationPrecipitated 7-Fluoro-imidazo [2,1-b]benzothiazole-3-carboxaldehyde (Formula L-3) was filtered
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-60c1f285ca854bfabc5e5a73ed670a40
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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