Chloroform → HCID 22041461, compound

HRID 1790232Notes

Reaction equation

HRID 1790232 reaction equation
[CH:1]([Cl:4])(Cl)Cl.[F:5][C:6]1[CH:36]=[CH:35][C:9]2[S:10][C:11]([S:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[S:25][CH:26]=[C:27](CO)[N:28]=4)=[CH:20][C:19]=3[S:31]([CH3:34])(=[O:33])=[O:32])(=[O:16])=[O:15])=[C:12]([CH3:13])[C:8]=2[CH:7]=1.S(Cl)(Cl)=O>C(N(CC)CC)C>[Cl:4][CH2:1][C:27]1[N:28]=[C:24]([C:21]2[CH:22]=[CH:23][C:18]([NH:17][S:14]([C:11]3[S:10][C:9]4[CH:35]=[CH:36][C:6]([F:5])=[CH:7][C:8]=4[C:12]=3[CH3:13])(=[O:15])=[O:16])=[C:19]([S:31]([CH3:34])(=[O:32])=[O:33])[CH:20]=2)[S:25][CH:26]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl Chloride2×HCID 10128443HCID 10128443, compound

Product 1

HCID 22041461HCID 22041461, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into 20 mL of chloroform was suspended 159 mg of Compound 63, and 47 μL of thionyl chloride was added at 0° C., followed by 21 hours of stirring at room temperature. Further, 1 mL of thionyl chloride was added, followed by 1 hour of heating under refluxing. After 2 mL of triethylamine was added at 0° C. and the mixture was stirred for 3 hours, the reaction was terminated with 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, successively and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform) to obtain 104 mg of the title compound as light brown powder.

Workup

  1. additionwas added at 0° C.
  2. waitfollowed by 1 hour
  3. temperatureof heating
  4. temperatureunder refluxing
  5. stirringthe mixture was stirred for 3 hours
  6. customthe reaction was terminated with 1 mol/L hydrochloric acid
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with water and saturated brine
  9. dry with materialsuccessively and then dried over anhydrous sodium sulfate
  10. customThe solvent was removed by evaporation under reduced pressure
  11. customthe resulting residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-8d1b90adae4349a2acadac9aa9c5d382
Source dataset
uspto-grants-2006_07
Patent number
US07071220B2

Reaction notes

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