HCID 15086004, compound → HCID 21256462, compound

HRID 635859Notes

Reaction equation

HRID 635859 reaction equation
[N:1]1[CH:2]=[C:3]([CH2:13][OH:14])[N:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:6][C:5]=12>CN(C=O)C.C1(C)C=CC=CC=1.O=[Mn]=O>[N:1]1[CH:2]=[C:3]([CH:13]=[O:14])[N:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:6][C:5]=12

Participants

5

Reactant 1

HCID 15086004HCID 15086004, compound

Product 1

HCID 21256462HCID 21256462, compoundYield 101%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of imidazo[2,1-b]benzothiazole-3-methanol (Formula J-2) (2.0 g) in DMF (30 mL) and toluene (200 mL) was treated with MnO2 (4.5 g) and the mixture was azeotropically distilled for 4.5 hours. A second change of MnO2 (2.0 g) and distillation for 1 hour completed the conversion. The suspension was filtered, the combined filtrate and ethyl acetate washes of the cake were concentrated, the residue was diluted with water, and filtered to yield imidazo[2,1-b]benzothiazole-3-carboxaldehyde (Formula J-3) (2.0 g). Crude imidazo[2,1-b]benzothiazole-3-carboxaldehyde (Formula J-3) was used without further purification.

Workup

  1. distillationthe mixture was azeotropically distilled for 4.5 hours
  2. distillationA second change of MnO2 (2.0 g) and distillation for 1 hour
  3. filtrationThe suspension was filtered
  4. concentrationthe combined filtrate and ethyl acetate washes of the cake were concentrated
  5. additionthe residue was diluted with water
  6. filtrationfiltered

Sources & evidence

ORD record
ord-79aad8076cb54545a3b087e9f2968385
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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