Hydrochloric Acid → HCID 18003017, compound

HRID 478849Notes

Reaction equation

HRID 478849 reaction equation
BrBr.[ClH:3].[CH3:4][C:5]1[N:12]2[C:8](=[N:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=32)[S:7][C:6]=1[C:17](=[O:19])[CH3:18]>C(O)(=O)C>[ClH:3].[ClH:3].[CH2:11]([N:12]([CH2:5][CH3:4])[CH2:18][C:17]([C:6]1[S:7][C:8]2=[N:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]2[C:5]=1[CH3:4])=[O:19])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24408BromineHCID 2988560HCID 2988560, compound

Product 1

HCID 18003017HCID 18003017, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Bromine (1 ml) and concentrated hydrochloric acid (2 ml) were added to an acetic acid (200 ml) solution of 1-(3-methylthiazolo[3,2-a]benzoimidazol-2-yl)ethanone (Can. J. Chem., 45 (23), 2903-2912 (1967)) (2.3 g), and the mixture was stirred at 90° C. for 30 minutes. The reaction solution was cooled to room temperature, and the thus formed precipitate was collected by filtration and washed with EtOAc. Under ice-cooling, a 1.2 g portion of this was added to an acetonitrile (30 ml) solution of diethylamine (3 ml), and the mixture was stirred at the same temperature for 30 minutes. The reaction solution was mixed with water, extracted with EtOAc, washed with water and saturated brine and dried with anhydrous Na2SO4, and the solvent was evaporated under a reduced pressure. The resulting residue was purified by a column chromatography (eluent; Hex:EtOAc=2:1˜1:1) and further converted into hydrochloride in the usual way to obtain the title compound (355 mg).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationthe thus formed precipitate was collected by filtration
  3. washwashed with EtOAc
  4. temperatureUnder ice-cooling
  5. additiona 1.2 g portion of this was added to an acetonitrile (30 ml) solution of diethylamine (3 ml)
  6. stirringthe mixture was stirred at the same temperature for 30 minutes
  7. additionThe reaction solution was mixed with water
  8. extractionextracted with EtOAc
  9. washwashed with water and saturated brine
  10. dry with materialdried with anhydrous Na2SO4
  11. customthe solvent was evaporated under a reduced pressure
  12. customThe resulting residue was purified by a column chromatography (eluent; Hex:EtOAc=2:1˜1:1)

Sources & evidence

ORD record
ord-29e91d6f95e64e95a86dd75558719cf9
Source dataset
uspto-grants-2003_11
Patent number
US06642264B1

Reaction notes

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