Dimethyl Sulfoxide → HCID 86735484, compound

HRID 616563Notes

Reaction equation

HRID 616563 reaction equation
[SH-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18](=[N:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1OC)[O-:19].[CH3:29]S(C)=O>>[CH3:29][O:19][N:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH3:10])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24477Sodium ThiosulfateHCID 28015Sodium hydrosulfideHCID 353717Diazene, bis(2-methoxyphenyl)-, 1-oxide

Product 1

HCID 86735484HCID 86735484, compoundYield 88%

Conditions

Temperature
75 °C

Procedure

85 Parts of an aqueous solution of 36 percent technical sodium hydrosulphide, containing 1 percent sodium thiosulphate, were added to a mixture comprising 51.6 parts of 2,2'-dimethoxy azoxybenzene in 100 parts dimethyl sulfoxide at 60° within one hour. Subsequently, the temperature of the reaction mixture was raised to 75° C and maintained at 70° C-75° C for 2 1/2 hours. The pH of the reaction mixture was maintained between 9.5 and 10.0. After this period the starting material was shown to be entirely reduced. Then the reaction mixture was cooled down to 0° C, the separated product was filtered off and washed with water until alkali-free. After drying below 70° C, 43.0 parts of high quality 2,2'-dimethoxyhydrazobenzene of a melting point of 100° C to 102° C were obtained, this repesenting a yield of 88 percent of the theory.

Workup

  1. additionwere added to a mixture
  2. customat 60°
  3. customwithin one hour
  4. temperaturemaintained at 70° C-75° C for 2 1/2 hours
  5. temperatureThe pH of the reaction mixture was maintained between 9.5 and 10.0
  6. waitAfter this period the starting material was shown
  7. temperatureThen the reaction mixture was cooled down to 0° C
  8. filtrationthe separated product was filtered off
  9. washwashed with water until alkali-free
  10. customAfter drying below 70° C

Sources & evidence

ORD record
ord-2806829d63d24ed78439b16ce875f255
Source dataset
uspto-grants-1978_02
Patent number
US04075198

Reaction notes

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