Water → 4-((4-aminophenyl)azo)-N,N-dimethylaniline

HRID 65174Notes

Reaction equation

HRID 65174 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.S.[Na].O>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 172254'-Nitro-4-dimethylaminoazobenzeneHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 108724-((4-aminophenyl)azo)-N,N-dimethylanilineYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 88.1 g of 4-nitro-4'-(dimethylamino)azobenzene in 1080 ml of ethanol was heated to slight reflux while stirring, treated dropwise within 35 minutes with 1017 g of 25% sodium hydrogen sulphide solution and then stirred at slight reflux for another 1 hour. The mixture was cooled to room temperature, treated with 2120 ml of water and suction filtered. The residue was washed with water/ethanol (vol. 3:1) and dried at 50° C. in vacuo, yielding 55.7 g of 4-amino-4'-(dimethylamino)azobenzene; m.p. 182.5°-187.4° C.

Workup

  1. temperaturewas heated
  2. temperatureto slight reflux
  3. stirringstirred
  4. temperatureat slight reflux for another 1 hour
  5. filtrationfiltered
  6. washThe residue was washed with water/ethanol (vol. 3:1)
  7. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-962207b8cbde479cbf8b07de94cf4b57
Source dataset
uspto-grants-1986_09
Patent number
US04613208

Reaction notes

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