Sodium Thiosulfate → HCID 54543206, compound

HRID 1733866Notes

Reaction equation

HRID 1733866 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH3:18])[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2].S([O-])([O-])(=O)=O.[Al+3].S([O-])([O-])(=O)=O.S([O-])([O-])(=O)=O.[Al+3].[S:36]([O-])([O-:39])(=[O:38])=[S:37].[Na+].[Na+].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>Cl.O.C(O)(=O)C>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH3:18])=[CH:12][C:13]=1[S:36]([OH:39])(=[O:38])=[S:37]

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 24850Aluminum SulfateHCID 25408Sodium DichromateHCID 19438635HCID 19438635, compound

Product 1

HCID 54543206HCID 54543206, compoundYield 89.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

N-(4-Ethoxycarbonylbutyl)-N-methyl-p-phenylenediamine (1.7 g) was dissolved in 1N hydrochloric acid (13.6 ml) and to the solution was added a solution of aluminium sulfate 14-18 hydrate in water (10 ml). The mixture was ice-cooled. A solution of sodium thiosulfate 5 hydrate (2 g) in water (8 ml) was added thereto and further a solution of sodium dichromate 2 hydrate (0.798 g) in water (5 ml) was added dropwise. The resulting mixture was stirred for 30 minutes under ice-cooling. Then acetic acid (0.6 ml) was added and the mixture was further stirred at room temperature for 2 hours. The reaction mixture was concentrated to dryness. The concentrate was made alkaline with an aqueous sodium bicarbonate and insoluble materials were filtered off. The filtrate was adjusted to pH 4 with acetic acid, concentrated to about 50 ml and cooled. The resulting crystalline precipitate was filtered off, washed with cold water and dried to obtain the desired compound (2.1 g).

Workup

  1. temperaturecooled
  2. temperaturecooling
  3. stirringthe mixture was further stirred at room temperature for 2 hours
  4. concentrationThe reaction mixture was concentrated to dryness
  5. filtrationwere filtered off
  6. concentrationconcentrated to about 50 ml
  7. temperaturecooled
  8. filtrationThe resulting crystalline precipitate was filtered off
  9. washwashed with cold water
  10. customdried

Sources & evidence

ORD record
ord-aa0d944d3ba04af783ce5dac9c32514f
Source dataset
uspto-grants-1996_07
Patent number
US05532171

Reaction notes

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