Hydrochloric Acid → HCID 19834627, compound

HRID 1087694Notes

Reaction equation

HRID 1087694 reaction equation
[H][H].O.[N+:4]([C:7]1[C:8]([O:22][CH2:23][CH2:24][CH2:25][OH:26])=[C:9]([Cl:21])[CH:10]=[C:11]([N+:18]([O-])=O)[C:12]=1[O:13][CH2:14][CH2:15][CH2:16][OH:17])([O-])=O.Cl>C(O)C.[Fe].C(OCC)(=O)C.C(O)(=O)C>[ClH:21].[OH:26][CH2:25][CH2:24][CH2:23][O:22][C:8]1[C:7]([NH2:4])=[C:12]([O:13][CH2:14][CH2:15][CH2:16][OH:17])[C:11]([NH2:18])=[CH:10][C:9]=1[Cl:21]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 19751957HCID 19751957, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19834627HCID 19834627, compound

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

250 g of powdered iron which had been reduced with hydrogen were added to 700 ml of water containing 10 ml of acetic acid which had been previously heated to 95° C., and 0.34 mole (119 g) of 3,5-bisnitro-2,4-bis-(γ-hydroxypropoxy)chlorobenzene was added gradually with stirring. Upon completion of the additions, the reaction mixture was maintained for 10 additional minutes at 95° C. After cooling, 1 liter of ethyl acetate was added. The reaction mixture was filtered off in order to remove the iron slurries. The ethyl acetate phase which was separated from the aqueous phase, was, after washing with water and drying over sodium sulphate evaporated off to dryness. The solids content obtained in this manner was taken up with a hydrochloric acid solution in absolute ethanol. The expected product precipitated. After thorough draining followed by drying, analysis of the product obtained gave the following results:

Workup

  1. temperatureUpon completion of the additions, the reaction mixture was maintained for 10 additional minutes at 95° C
  2. temperatureAfter cooling
  3. filtrationThe reaction mixture was filtered off in order
  4. customto remove the iron slurries
  5. customThe ethyl acetate phase which was separated from the aqueous phase
  6. washafter washing with water
  7. dry with materialdrying over sodium sulphate
  8. customevaporated off to dryness
  9. customThe solids content obtained in this manner
  10. customThe expected product precipitated
  11. customby drying
  12. customanalysis of the product obtained
  13. customgave the
  14. customfollowing results

Sources & evidence

ORD record
ord-a9d4a9e7eab34b2c936e2c4d19736e3d
Source dataset
uspto-grants-1990_10
Patent number
US04960432

Reaction notes

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