Acetic Acid → HCID 19751973, compound

HRID 1607485Notes

Reaction equation

HRID 1607485 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].[ClH:23].[NH2:8][C:11]1[C:12]([O:24][CH2:25][CH3:26])=[C:13]([Cl:23])[CH:14]=[C:15]([NH2:20])[C:16]=1[O:17][CH2:18][CH3:19]

Participants

7

Reactant 4

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

Product 1

HCID 19751973HCID 19751973, 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 had previously been heated to 80° C., and then 0.3 mole (87 g) of 3,5-dinitro-2,4-diethoxychlorobenzene was added gradually, 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. washThe ethyl acetate phases joined together were 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-a9544eada1094080ad8d949edc553a0b
Source dataset
uspto-grants-1989_09
Patent number
US04865618

Reaction notes

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