Methanol → [(3,4-Diaminophenyl)sulfanyl]acetonitrile

HRID 1414796Notes

Reaction equation

HRID 1414796 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]#[N:11])=[CH:4][C:3]=1[N+:12]([O-])=O.CO>[Fe].O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]#[N:11])=[CH:4][C:3]=1[NH2:12]

Participants

5

Reactant 2

HCID 887MethanolHCID 20362816[(4-Amino-3-nitrophenyl)sulfanyl]acetonitrile

Product 1

HCID 20362813[(3,4-Diaminophenyl)sulfanyl]acetonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent

Procedure

4.1 G. of 1-amino-2-nitro-4-cyanomethylthiobenzene in 60 ml. of methanol and 12 ml. of water is treated with 1.25 g. of ferrous sulfate and 3.3 g. of iron powder at reflux. After 2 hours, 1.25 g. of ferrous sulfate and 3.3 g. of iron powder are added and heating is continued for 4 hours. The mixture is poured into 600 ml. of hot tetrahydrofuran and filtered. 1,2-Diamino-4-cyanomethylthiobenzene is obtained from the filtrate by evaporation.

Workup

  1. temperatureheating
  2. waitis continued for 4 hours
  3. additionThe mixture is poured into 600 ml
  4. filtrationof hot tetrahydrofuran and filtered

Sources & evidence

ORD record
ord-06995c31d3304e0596f3dfc6b17ba0a4
Source dataset
uspto-grants-1977_01
Patent number
US04002640

Reaction notes

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