Water → HCID 22273236, compound

HRID 1064363Notes

Reaction equation

HRID 1064363 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.[N:13]1([CH2:19][CH2:20][OH:21])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(O)CCCCC1>[Cl:1][C:2]1[C:8]([N:16]2[CH2:17][CH2:18][N:13]([CH2:19][CH2:20][OH:21])[CH2:14][CH2:15]2)=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 76771-(2-Hydroxyethyl)piperazineHCID 10340Sodium CarbonateHCID 811494,5-Dichloro-2-nitroaniline

Product 1

HCID 22273236HCID 22273236, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 7966CyclohexanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 4.14 g of 4,5-dichloro-2-nitroaniline and 2.73 g of 1-piperazine ethanol in 20 ml of cyclohexanol, 2.65 g of sodium carbonate was added, and stirred for 14 hours at 150° C. After cooling the reaction liquid to room temperature, water was added thereto, followed by extraction with chloroform. The chloroform layer was dried on anhydrous magnesium sulfate and the solvent was distilled off. The residue was separated and purified on silica gel column chromatography (chloroform/methanol=10/1) to provide 5.31 g of the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe reaction liquid to room temperature
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe chloroform layer was dried on anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was separated
  7. custompurified on silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-05c8e6d0d5774895b7fc1720672a69b8
Source dataset
uspto-grants-2005_11
Patent number
US06969712B2

Reaction notes

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