Hydrochloric Acid → HCID 21392401, compound

HRID 461763Notes

Reaction equation

HRID 461763 reaction equation
[F:1][C:2]([C:8]1[CH:9]=[C:10]([N+:14]([O-])=O)[CH:11]=[CH:12][CH:13]=1)([Cl:7])[C:3]([F:6])([Cl:5])[Cl:4].Cl>C(O)C>[F:1][C:2]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[NH2:14])([Cl:7])[C:3]([F:6])([Cl:5])[Cl:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21392415HCID 21392415, compound

Product 1

HCID 21392401HCID 21392401, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

104.4 G. of 3-(1,2-difluoro-1,2,2-trichloroethyl)-nitrobenzene is added over 10 min. to a solution of 325 g. of crystalline stannous chloride (SnCl2 . 2H2O) in 325 g. of concentrated HCl and 325 g. of ethanol with vigorous stirring, maintaining the temperature at 50° C. Stirring is continued for 3 additional hours. It is cooled in ice, and the precipitate collected by filtration. The solids are then suspended in 500 ml. water and 500 ml. of CH2Cl2, the mixture is cooled in ice and made basic by the addition of 50% aqueous NaOH until almost all solids are dissolved. The methylenechloride layer is separated, washed with water, dried with Na2SO4 and concentrated in vacuo to 75 g. of 3-(1,2-difluoro-1,2,2-trichloroethyl)-aniline as yellow oil.

Workup

  1. temperatureIt is cooled in ice
  2. filtrationthe precipitate collected by filtration
  3. temperatureof CH2Cl2, the mixture is cooled in ice
  4. additionmade basic by the addition of 50% aqueous NaOH until almost all solids
  5. dissolutionare dissolved
  6. customThe methylenechloride layer is separated
  7. washwashed with water
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated in vacuo to 75 g

Sources & evidence

ORD record
ord-0d3c9b2227f5457db24127f0ab37b4f9
Source dataset
uspto-grants-1977_12
Patent number
US04064239

Reaction notes

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