HCID 21256507, compound → HCID 21256465, compound

HRID 635867Notes

Reaction equation

HRID 635867 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[N:7]3[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[C:8]3[S:9][C:5]=2[CH:4]=1>CN(C=O)C.C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[N:7]3[C:12]([CH:13]=[O:14])=[CH:11][N:10]=[C:8]3[S:9][C:5]=2[CH:4]=1

Participants

5

Reactant 1

HCID 21256507HCID 21256507, compound

Product 1

HCID 21256465HCID 21256465, compoundYield 95.6%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-Methoxy-imidazo[2,1-b]benzothiazole-3-methanol (Formula M-2) (4.0 g) in DMF (25 mL) was diluted with toluene (200 mL) and the warm solution was treated with MnO2 (8.84 g). The suspension was azeotropically distilled for 4 hours, cooled to 50°, and filtered. The combined filtrate and toluene washes were concentrated and the concentrate was diluted with water. Precipitated 7-Methoxy-imidazo[2,1-b]benzothiazole-3-carboxaldehyde (Formula M-3) (3.8 g) was filtered and recrystallized from acetonitrile to yield pure 7-Methoxy-imidazo [2,1-b]benzothiazole-3-carboxaldehyde (Formula M-3) (3.79 g), m.p. 168-169°.

Workup

  1. distillationThe suspension was azeotropically distilled for 4 hours
  2. temperaturecooled to 50°
  3. filtrationfiltered
  4. concentrationThe combined filtrate and toluene washes were concentrated
  5. additionthe concentrate was diluted with water
  6. filtrationPrecipitated 7-Methoxy-imidazo[2,1-b]benzothiazole-3-carboxaldehyde (Formula M-3) (3.8 g) was filtered
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-48770c2edb9f48eb91e30ec5cd6ab74e
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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