Trichloroacetyl chloride → 2,9-Dimethyl-3-trichloroacetylimidazo[1,2-a]benzimidazole

HRID 1683721Notes

Reaction equation

HRID 1683721 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[CH3:8][C:9]1[N:10]=[C:11]2[N:15]([CH:16]=1)[C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[N:12]2[CH3:21]>C1(C)C(C)=CC=CC=1>[CH3:8][C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:3](=[O:4])[C:2]([Cl:7])([Cl:6])[Cl:1])[C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[N:12]2[CH3:21]

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 8282692,4-Dimethylimidazo[1,2-a]benzimidazole

Product 1

HCID 190408122,9-Dimethyl-3-trichloroacetylimidazo[1,2-a]benzimidazole

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Pour 5.45 g (30 mmol) of freshly distilled trichloroacetyl chloride dropwise into a boiling solution of 2,9-dimethylimidazo[1,2-a]benzimidazole(3.7 g; 20 mmol) obtained as described in Khim. Geterotsikl Soedin, 86, (7), 918-925--in 50 ml of xylene, with vigorous stirring, over a period of 20 to 30 minutes. The mixture is then heated at reflux for wo hours until the product which has initially precipitated is completely dissolved. Cool and filter. Concentrate the mother liquors and add petroleum ehter. Combie with the precipitate obtained earlier and repeat the operation. The combined precipitates are treated with an aqueous solution of sodium hydrogen carbonate and then recrystallised from ethyl acetate.

Workup

  1. customobtained
  2. temperatureThe mixture is then heated
  3. temperatureat reflux for wo hours until the product which
  4. customhas initially precipitated
  5. dissolutionis completely dissolved
  6. temperatureCool
  7. filtrationfilter
  8. concentrationConcentrate the mother liquors
  9. additionadd petroleum ehter
  10. customCombie with the precipitate obtained earlier
  11. customThe combined precipitates
  12. additionare treated with an aqueous solution of sodium hydrogen carbonate
  13. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-771fdf85b83348c9a668a315d8e78fef
Source dataset
uspto-grants-1997_06
Patent number
US05639756

Reaction notes

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