HCID 157047, compound → HCID 53951882, compound

HRID 1168680Notes

Reaction equation

HRID 1168680 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]>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

3

Reactant 1

HCID 157047HCID 157047, compound

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 α-chloroethyl chlorofonnate (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. additionwas treated with α-chloroethyl chlorofonnate (98 μL 0.907 mmol)
  2. temperaturerefluxed overnight
  3. customThe solvent was then removed in vacuo and 10 mL of methanol
  4. additionwas added
  5. temperaturerefluxed for 30 minutes
  6. customremoval of the solvent
  7. extractionthe residue was extracted into methylene chloride
  8. washwashed with saturated aqueous sodium carbonate (Na2CO3) and saturated brine
  9. dry with materialdried with magnesium sulfate
  10. concentrationconcentrated to a foam

Sources & evidence

ORD record
ord-d14ff4d9d9ba4af7a2698a22d91d8e2c
Source dataset
uspto-grants-2003_09
Patent number
US06627627B2

Reaction notes

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