Methanol → HCID 86735484, compound

HRID 616559Notes

Reaction equation

HRID 616559 reaction equation
[SH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11](=[N:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1OC)[O-:12].[CH3:22]O>>[CH3:22][O:12][N:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH3:3])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 28015Sodium hydrosulfideHCID 353717Diazene, bis(2-methoxyphenyl)-, 1-oxide

Product 1

HCID 86735484HCID 86735484, compoundYield 72%

Procedure

90 parts of an aqueous solution of technical sodium hydrosulfide containing 35 percent NaHS and 4 percent NasS2O3 were added to a mixture comprising 51.6 parts of 2,2'-dimethoxyazoxybenzene in 155 parts methanol at room temperature within 5 hours. Subsequently, the reaction mixture was refluxed at 70° C to 75° C for 2 1/2 hours while the pH was maintained between 8.5 and 9.4. After this period the absence of the starting material was confirmed and the reaction mixture was cooled down to 0° C to 5° C, the reduced product that precipitated filtered off and washed with water until alkali-free. After drying below 70° C, 35 parts of 2,2'-dimethoxyhydrazobenzene of a melting point of 100° C to 102° C were obtained, this representing a commercially acceptible grade in a yield of 72 percent of theory.

Workup

  1. customat room temperature
  2. customwithin 5 hours
  3. temperatureSubsequently, the reaction mixture was refluxed at 70° C to 75° C for 2 1/2 hours while the pH
  4. temperaturewas maintained between 8.5 and 9.4
  5. waitAfter this period the absence of the starting material was confirmed
  6. temperaturethe reaction mixture was cooled down to 0° C to 5° C
  7. customthe reduced product that precipitated
  8. filtrationfiltered off
  9. washwashed with water until alkali-free
  10. customAfter drying below 70° C

Sources & evidence

ORD record
ord-4d0ecd5f839e43cd90baa059658b848a
Source dataset
uspto-grants-1978_02
Patent number
US04075198

Reaction notes

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