Acetic Acid → HCID 13173181, compound

HRID 980357Notes

Reaction equation

HRID 980357 reaction equation
[CH3:1][NH:2][CH3:3].C=O.[C:6](O)(=O)C.[C:10]([C:14]1[CH:15]=[C:16]([C:25]2[N:26]=[C:27]3[N:31]([CH:32]=2)[CH2:30][CH2:29][S:28]3)[CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])([CH3:13])([CH3:12])[CH3:11]>O1CCOCC1>[CH3:1][N:2]([CH2:6][C:32]1[N:31]2[C:27]([S:28][CH2:29][CH2:30]2)=[N:26][C:25]=1[C:16]1[CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]([OH:20])=[C:14]([C:10]([CH3:11])([CH3:12])[CH3:13])[CH:15]=1)[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 13173170HCID 13173170, compound

Product 1

HCID 13173181HCID 13173181, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixed solution of 0.9 g of an aqueous 40% dimethylamine solution, 0.5 g of an aqueous 35% formaldehyde solution, 1.5 ml of acetic acid, and 5 ml of dioxane was added 0.66 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole and the resulting mixture was refluxed for 6 hours. The reaction mixture was concentrated under reduced pressure and the residue was mixed with 20 ml of an aqueous 10% potassium carbonate solution and extracted with chloroform. The extract was dried and concentrated, and the residue thus formed was purified by silica gel chromatography using chloroform as the eluent and further recrystallized from aqueous ethanol to provide 0.3 g of 5-dimethylaminomethyl-6-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole.1/4H2O.

Workup

  1. temperaturethe resulting mixture was refluxed for 6 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was mixed with 20 ml of an aqueous 10% potassium carbonate solution
  4. extractionextracted with chloroform
  5. customThe extract was dried
  6. concentrationconcentrated
  7. customthe residue thus formed
  8. customwas purified by silica gel chromatography
  9. customfurther recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-abc82d99fa2a483ca143c477abcc949d
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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