Ethanol → 3,4-Diaminophenyl thiocyanate

HRID 745670Notes

Reaction equation

HRID 745670 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.[Cl-].[NH4+]>[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

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 1046774-Amino-3-nitrophenyl thiocyanate

Product 1

HCID 132100373,4-Diaminophenyl thiocyanateYield 74%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

To a suspension of 2-nitro-4-thiocyanato-aniline, 22.3 g. of powdered iron, 50 ml. of 96% ethanol and 50 ml. of water a solution of 2.2 g. of ammonium chloride and 15 ml. of water is added dropwise under stirring at the boiling point of the mixture. Stirring is continued for a further 15 minutes, whereupon the reaction mixture is filtered until warm. To the filtrate 250 ml. of water are added. After cooling the precipitated crystals are filtered off. Thus 12.2 g. of 4-thiocyanato-1,2-diaminobenzene are obtained. Yield: 74%. M.p.: 108°-110° C.

Workup

  1. stirringStirring
  2. filtrationis filtered
  3. temperatureuntil warm
  4. additionof water are added
  5. temperatureAfter cooling the precipitated crystals
  6. filtrationare filtered off

Sources & evidence

ORD record
ord-ea596646dd2e42329452a39af65429be
Source dataset
uspto-grants-1986_07
Patent number
US04599428

Reaction notes

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