Dichloromethane → Aniline, N,N-bis(2-chloroethyl)-p-fluoro-

HRID 1282123Notes

Reaction equation

HRID 1282123 reaction equation
O[CH2:2][CH2:3][N:4]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH2:5]CO.S(Cl)([Cl:17])=O.C(=O)([O-])O.[Na+].[CH2:24]([Cl:26])Cl>>[Cl:17][CH2:2][CH2:3][N:4]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH2:5][CH2:24][Cl:26]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 184230372-[(4-Fluorophenyl)(2-hydroxyethyl)amino]ethan-1-ol

Product 1

HCID 30941Aniline, N,N-bis(2-chloroethyl)-p-fluoro-

Procedure

To a solution of N,N-bis(2-hydroxyethyl)-4-fluorophenylamine (9.2 g) in methylene chloride (92 ml) was added dropwise thionyl chloride (7.1 ml) over 10 min under ice-cooling. The mixture was stirred at room temperature for 1 hr and the reaction mixture was further refluxed for 1.5 hr. The mixture was poured into aqueous sodium hydrogencarbonate to make it alkaline and the organic layer was separated. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=10:1) to give the title compound (4.88 g) as an organge oil.

Workup

  1. temperaturecooling
  2. temperaturethe reaction mixture was further refluxed for 1.5 hr
  3. customthe organic layer was separated
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-c5ae34b312b64a0d8074a88c4843bd0e
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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