Azoxybenzene → 1,2-Bis(3-chlorophenyl)hydrazine

HRID 616560

Reaction equation

HRID 616560 reaction equation
[SH-].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[N+:11](=[N:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1Cl)[O-].[N+](C1C=CC=CC=1)(=NC1C=CC=CC=1)[O-]>CO>[Cl:10][C:7]1[CH:8]=[CH:9][CH:4]=[C:5]([NH:11][NH:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][CH:15]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 10316AzoxybenzeneHCID 28015Sodium hydrosulfideHCID 14205666Diazene, bis(2,5-dichlorophenyl)-, 1-oxide

Product 1

HCID 2579191,2-Bis(3-chlorophenyl)hydrazineYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

85 Parts of an aqueous solution of technical sodium hydrosulfide containing 35 percent NaHS and 9 percent Na2S 2 O3 were added to a mixture comprising 65.4 parts of 2,2'-dichlor-5,5'-dichloroazoxybenzene in 196 parts of methanol at room temperature within 90 minutes. The reaction mixture was then refluxed at 70° C to75° C for a period of 5 hours. The pH had been kept between 9 and 9.4. After this period the starting azoxybenzene was shown to be all consumed and the reaction mixture was cooled down to 0° C to 5° C, and the resulting precipitate filtered off and washed with water until alkali-free. After drying below 70° C 48 parts of 2,2'-dichloro,-5,5'-dichlorohydrazobenzene of a melting point of 116° C were obtained, this representing yield of 76 percent of the theory.

Workup

  1. customat room temperature
  2. customwithin 90 minutes
  3. customall consumed
  4. temperaturethe reaction mixture was cooled down to 0° C to 5° C
  5. filtrationthe resulting precipitate filtered off
  6. washwashed with water until alkali-free
  7. customAfter drying below 70° C 48 parts of 2,2'-dichloro

Sources & evidence

ORD record
ord-16d0f3124ce94af09b5ea96fa48dc704
Source dataset
uspto-grants-1978_02
Patent number
US04075198

Linked notes

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