Water → HCID 21911983, compound

HRID 1245437Notes

Reaction equation

HRID 1245437 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:5]([NH2:6])=[C:4]([F:12])[C:3]=1F.[CH2:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:5]([NH2:6])=[C:4]([F:12])[C:3]=1[N:19]1[CH2:20][CH2:21][N:16]([CH2:14][CH3:15])[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 17897329HCID 17897329, compound

Product 1

HCID 21911983HCID 21911983, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 768 mg of 4-chloro-2,3-difluoro-6-nitroaniline (which was prepared by the method described in WO 98/56761 or WO 98/35977) and 629 mg of 1-ethylpiperazine in 5 ml of dimethylsulfoxide, 1.00 g of potassium carbonate was added, followed by 2 hours' stirring at 50° C. Water was added to the reaction liquid, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried on anhydrous magnesium sulfate, and the solvent was distilled off. The residue was separated and purified on silica gel column chromatography (chloroform/methanol=50/1) to provide 704 mg of the title compounds.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried on anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was separated
  7. custompurified on silica gel column chromatography (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-a44dc534961245dab70e818790206b4c
Source dataset
uspto-grants-2006_10
Patent number
US07125877B2

Reaction notes

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