2-Methoxyethanol → HCID 23359030, compound

HRID 232650Notes

Reaction equation

HRID 232650 reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([F:13])[C:3]=1[CH3:14].COCCO.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>O.C(N(CC)CC)C>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:2]2[C:7]([F:8])=[C:6]([CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([F:13])[C:3]=2[CH3:14])[CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 80192-MethoxyethanolHCID 531671-MethylpiperazineHCID 23358998HCID 23358998, compound

Product 1

HCID 23359030HCID 23359030, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

To 2,3,6-trifluoro-4-methyl-5-nitrotoluene (1.9 g) are added 2-methoxyethanol (9.9 ml), water (1.1 ml), N-methylpiperazine (4.1 ml) and triethylamine (5.2 ml) and the mixture is refluxed for 25 hours. After the reaction is completed, water is added and the resultant 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 (dichloromethane: methanol=40:1) to give 2-(4-methyl-1-piperazinyl)-3,6-difluoro-4-methyl-5-nitrotoluene (1.73 g).

Workup

  1. temperaturethe mixture is refluxed for 25 hours
  2. extractionthe resultant 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 (dichloromethane: methanol=40:1)

Sources & evidence

ORD record
ord-dd48b8fa89aa494daf3de3a8cbca1db2
Source dataset
uspto-grants-1997_01
Patent number
US05591744

Reaction notes

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