HCID 21256487, compound → HCID 21256443, compound

HRID 635861Notes

Reaction equation

HRID 635861 reaction equation
[CH3:1][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>C1(C)C=CC=CC=1.O1CCOCC1.O=[Mn]=O>[CH3:1][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 21256487HCID 21256487, compound

Product 1

HCID 21256443HCID 21256443, compoundYield 68.9%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 7-Methyl-imidazo[2,1-b]benzothiazole-3-methanol (Formula K-2) (0.82 g) in hot toluene (100 mL) was diluted with dioxane (10 mL) to effect dissolution of 7-Methyl-imidazo [2,1b]benzothiazole-3-methanol (Formula K-2). The solution was treated with activated MnO2 (1.64 g) and azeotropically distilled for 1.25 hours. The suspension was filtered, the cake was washed with hot ethyl acetate, and the filtrate was evaporated to a crystalline solid (0.69 g). Crystallization from isopropanol gave pure 7-Methyl-imidazo[2,1-b]benzothiazole-3-carboxaldehyde (Formula K-3) (0.56 g), m.p. 170-171°.

Workup

  1. distillationazeotropically distilled for 1.25 hours
  2. filtrationThe suspension was filtered
  3. washthe cake was washed with hot ethyl acetate
  4. customthe filtrate was evaporated to a crystalline solid (0.69 g)
  5. customCrystallization from isopropanol

Sources & evidence

ORD record
ord-8a89592296394798bfc2b9ac09b643c3
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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