HCID 157047, compound → HCID 53951882, compound

HRID 411984Notes

Reaction equation

HRID 411984 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][S:12][C:11](=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:22]3[CH2:27][CH2:26][N:25](C)[CH2:24][CH2:23]3)[C:10]2=[O:29])[CH:5]=[CH:6][C:7]=1[Cl:8].ClC(OC(Cl)C)=O>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][S:12][C:11](=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[C:10]2=[O:29])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 157047HCID 157047, compoundHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 53951882HCID 53951882, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Under a nitrogen atmosphere, a mixture of 4-(3,4-dichlorophenyl)-2-[2-(4-methylpiperazin-1-yl)-benzylidene]-thiomorpholin-3-one (338 mg, 0.756 mmol) in 9 mL of anhydrous 1,2-dichloroethane was treated with a-chloroethyl chloroformate (98 μL 0.907 mmol) and refluxed overnight. The solvent was then removed in vacuo and 10 mL of methanol was added and refluxed for 30 minutes. Following removal of the solvent, the residue was extracted into methylene chloride and washed with saturated aqueous sodium carbonate (Na2CO3) and saturated brine, dried with magnesium sulfate and concentrated to a foam. Flash chromatography using triethyl amine/methanol/ethyl acetate (1:2:97) gave the purified free base of the title compound.

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was then removed in vacuo and 10 mL of methanol
  3. additionwas added
  4. temperaturerefluxed for 30 minutes
  5. customremoval of the solvent
  6. extractionthe residue was extracted into methylene chloride
  7. washwashed with saturated aqueous sodium carbonate (Na2CO3) and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. concentrationconcentrated to a foam

Sources & evidence

ORD record
ord-f097d9ec54b84b55a46619bde83551d1
Source dataset
uspto-grants-2003_05
Patent number
US06562813B2

Reaction notes

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