Ethanol → 3,4-Diaminophenyl thiocyanate

HRID 745671Notes

Reaction equation

HRID 745671 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([S:11][C:12]#[N:13])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.C(O)C>[Fe].O>[S:11]([C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([NH2:1])[CH:10]=1)[C:12]#[N:13]

Participants

5

Reactant 2

HCID 702EthanolHCID 1046774-Amino-3-nitrophenyl thiocyanate

Product 1

HCID 132100373,4-Diaminophenyl thiocyanateYield 74.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

To a suspension of 2-nitro-4-thiocyanato-aniline, 22.3 g. of powdered iron, 40 ml. of 96% ethanol and 50 ml. of water a solution of 2,2 g. of ferrous(II)chloride and 4 ml. of water is added dropwise under stirring at the boiling point of the mixture. Stirring is continued for a further 10 minutes, whereupon the reaction mixture is filtered. To the filtrate 200 ml. of water are added. On cooling crystals precipitate, which are filtered off. Thus 12.3 g. of 4-thiocyanato-1,2-diamino-benzene are obtained. Yield: 74.5%. M.p.: 108°-110° C.

Workup

  1. stirringStirring
  2. filtrationis filtered
  3. additionof water are added
  4. temperatureOn cooling crystals precipitate, which
  5. filtrationare filtered off

Sources & evidence

ORD record
ord-838ba89fe883498aa8b39b42f1309930
Source dataset
uspto-grants-1986_07
Patent number
US04599428

Reaction notes

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