Acetic Acid → HCID 19834631, compound

HRID 1087691Notes

Reaction equation

HRID 1087691 reaction equation
[H][H].O.C(O)(=O)C.[N+:8]([C:11]1[C:12]([O:24][CH2:25][CH3:26])=[C:13]([Cl:23])[CH:14]=[C:15]([N+:20]([O-])=O)[C:16]=1[O:17][CH2:18][CH3:19])([O-])=O>[Fe].C(OCC)(=O)C>[ClH:23].[CH2:25]([O:24][C:12]1[C:11]([NH2:8])=[C:16]([O:17][CH2:18][CH3:19])[C:15]([NH2:20])=[CH:14][C:13]=1[Cl:23])[CH3:26]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 19751981HCID 19751981, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19834631HCID 19834631, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

170 g of powdered iron which had been reduced with hydrogen were added to 450 ml of water containing 8.5 ml of acetic acid which have previously been heated to 80° C., and then 0.3 mole (87 g) of 3,5-dinitro-2,4-diethoxychlorobenzene was then gradually added with stirring. Upon completion of the additions, the reaction mixture was maintained in a boiling water bath for 30 additional minutes. After cooling, the reaction mixture was centrifuged. The iron slurries were made to a paste again with ethyl acetate and the mother liquors were extracted with ethyl acetate. The ethyl acetate phases, joined together, were washed with water and then dried over Na2SO4. Upon addition of a hydrochloric acid solution in ethanol, the expected product precipitated. After thorough draining, it was washed with acetone. It was recrystallized from an aqueous-alcoholic solution of hydrochloric acid.

Workup

  1. temperatureUpon completion of the additions, the reaction mixture was maintained in a boiling water bath for 30 additional minutes
  2. temperatureAfter cooling
  3. extractionthe mother liquors were extracted with ethyl acetate
  4. washwere washed with water
  5. dry with materialdried over Na2SO4
  6. additionUpon addition of a hydrochloric acid solution in ethanol
  7. customthe expected product precipitated
  8. washAfter thorough draining, it was washed with acetone
  9. customIt was recrystallized from an aqueous-alcoholic solution of hydrochloric acid

Sources & evidence

ORD record
ord-8e18b867c5bb44de8a38b8f1e3a21ec8
Source dataset
uspto-grants-1990_10
Patent number
US04960432

Reaction notes

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