Acetic Acid → 4-(2,3-Dihydroimidazo[2,1-b]thiazol-5-yl)benzoic acid

HRID 2053779Notes

Reaction equation

HRID 2053779 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]2[C:6]([C:9]3[CH:16]=[CH:15]C(C#N)=[CH:11][CH:10]=3)=[CH:7][N:8]=[C:2]12.S(=O)(=O)(O)O.[C:22]([OH:25])(=[O:24])[CH3:23]>>[S:1]1[CH2:5][CH2:4][N:3]2[C:6]([C:9]3[CH:16]=[CH:15][C:23]([C:22]([OH:25])=[O:24])=[CH:11][CH:10]=3)=[CH:7][N:8]=[C:2]12

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 693096964-(2,3-Dihydroimidazo[2,1-b]thiazol-5-yl)benzonitrile

Product 1

HCID 693098594-(2,3-Dihydroimidazo[2,1-b]thiazol-5-yl)benzoic acid

Conditions

Temperature
100 °C

Procedure

2.00 g (8.80 mmol) of contaminated 4-(2,3-dihydroimidazo[2,1-b]thiazol-5-yl)benzonitrile is placed in 60 mL of 50% acetic acid solution at 0° C. and slowly combined with 30 mL of concentrated sulfuric acid with stirring and cooling in the ice bath. The reaction mixture is heated to 100° C. for 17 hours and then poured into 500 mL of ice water. The precipitated product formed is filtered off. The mother liquor is combined with sodium chloride and extracted with 300 mL of ethyl acetate, washed with saturated sodium chloride solution, dried with magnesium sulfate, and the solvent is distilled off. The residue remaining is combined with the above precipitate. Yield: 1.25 g (40% over 2 steps); Rf value: 0.55 (silica gel; ethyl acetate/ethanol=9:1); C12H10N2O2S (246.29); mass spectrum: (M+H)+=247

Workup

  1. customThe precipitated product formed
  2. filtrationis filtered off
  3. extractionextracted with 300 mL of ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-bb020c0080d5434fbd1ad1ec822dc035
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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