Hydrochloric Acid → HCID 70379639, compound

HRID 231368Notes

Reaction equation

HRID 231368 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][CH:14]([F:19])[C:15]([F:18])([F:17])[F:16])([O-])=O.Cl.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>[Fe].C(O)C>[NH2:1][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:13][CH:14]([F:19])[C:15]([F:17])([F:18])[F:16]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 86743225HCID 86743225, compound

Product 1

HCID 70379639HCID 70379639, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

89 g (0.31 moles) 2,4-dinitrotetrafluoroethoxybenzene, according to Step 1, 125 ml of a 50% aqueous solution of ethanol and 106.5 g iron powder (1.91 moles) are heated to 60°-70° C. in a water bath in a three-necked flask, which is equipped with a reflux condensor, drop addition funnel, stirrer and internal thermometer. Next, a solution of 6.5 ml concentrated hydrochloric acid in 30 ml 50% aqueous solution of ethanol is added dropwise so that the reduction takes place accompanied by reflux and gentle boiling. When the addition is terminated it is then stirred for 2 hours accompanied by reflux, allowed to cool and neutralized with alcoholic potassium hydroxide. Uncoverted iron and iron oxides are vacuum filtrated, accompanied by rewashing with ethanol. The solution is concentrated and the residue is distilled in the vacuum. 40 g (57% of the theoretical yield) of the free base is obtained which has a boiling range of 114°-117° C. at 106 Pascal. This product can be transformed into dihyrochloride with hydrochloric acid.

Workup

  1. temperatureare heated to 60°-70° C. in a water bath in a three-necked flask
  2. customwhich is equipped with a reflux condensor, drop addition funnel, stirrer and internal thermometer
  3. temperatureby reflux
  4. additionWhen the addition
  5. customis terminated it
  6. temperatureby reflux
  7. temperatureto cool
  8. filtrationfiltrated
  9. concentrationThe solution is concentrated
  10. distillationthe residue is distilled in the vacuum
  11. custom40 g (57% of the theoretical yield) of the free base
  12. customis obtained which

Sources & evidence

ORD record
ord-78b9ce0e702c451f9726952379ec3a4e
Source dataset
uspto-grants-1989_07
Patent number
US04845294

Reaction notes

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