Water → HCID 21911975, compound

HRID 1245440Notes

Reaction equation

HRID 1245440 reaction equation
[Cl:1][C:2]1[C:8](Cl)=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH2:13]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[C:8]([N:18]2[CH2:19][CH2:20][N:15]([CH2:13][CH3:14])[CH2:16][CH2:17]2)=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 811494,5-Dichloro-2-nitroaniline

Product 1

HCID 21911975HCID 21911975, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 20.0 g of 4,5-dichloro-2-nitroaniline and 16.0 g of 1-ethylpiperazine in 50 ml of dimethylsulfoxide, 20.0 g of potassium carbonate was added, followed by 2 hours' stirring at 120° C. Water was added to the reaction liquid, followed by extraction with diethyl ether. The diethyl ether layer was successively washed with water and saturated brine, dried on anhydrous magnesium sulfate, and the solvent was distilled off. The residue was recrystallized from chloroform-diethyl ether, to provide 20.3 g of the title compound.

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. washThe diethyl ether layer was successively washed with water and saturated brine
  3. dry with materialdried on anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was recrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-83a74b8e3a1044a58b0bca2e51451148
Source dataset
uspto-grants-2006_10
Patent number
US07125877B2

Reaction notes

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