Ethanol → HCID 23359031, compound

HRID 2396961Notes

Reaction equation

HRID 2396961 reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([F:13])[C:3]=1[CH3:14].C(O)C.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>O.C(N(CC)CC)C>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:2]2[C:7]([F:8])=[C:6]([Cl:9])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([F:13])[C:3]=2[CH3:14])[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 702EthanolHCID 531671-MethylpiperazineHCID 23358995HCID 23358995, compound

Product 1

HCID 23359031HCID 23359031, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

To 2,3,6-trifluoro-4-chloro-5-nitrotoluene (0.17 g) are added ethanol (3.3 ml), water (0.5 ml), N-methylpiperazine (0.45 ml) and triethylamine (0.56 ml) and the mixture is refluxed for 24 hours. After the reaction is completed, water is added to the reaction mixture and the mixture is extracted with diethyl ether, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the residue is purified by silica-gel column-chromatography (eluent; dichloromethane: methanol=20 : 1) to give 2-(4-methyl-1-piperazinyl)-3,6-difluoro-4-chloro-5-nitrotoluene (0.13 g).

Workup

  1. temperaturethe mixture is refluxed for 24 hours
  2. extractionthe mixture is extracted with diethyl ether
  3. washthe extract is washed with water
  4. customdried
  5. distillationThe solvent is distilled off under reduced pressure
  6. customthe residue is purified by silica-gel column-chromatography (eluent; dichloromethane: methanol=20 : 1)

Sources & evidence

ORD record
ord-40d4326fb4b54cc99073f5bb89638d1d
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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