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

HRID 1414794Notes

Reaction equation

HRID 1414794 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][C:11]#[N:12])=[CH:4][C:3]=1[N+:13]([O-])=O.CO>[Fe].O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][C:11]#[N:12])=[CH:4][C:3]=1[NH2:13]

Participants

5

Reactant 2

HCID 887MethanolHCID 203628123-[(4-Amino-3-nitrophenyl)sulfanyl]propanenitrile

Product 1

HCID 203628333-[(3,4-Diaminophenyl)sulfanyl]propanenitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent

Procedure

2.3 G. of 1-amino-2-nitro-4-(2-cyanoethylthio)benzene in 30 ml. of methanol and 6 ml. of water is treated with 2.5 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 four hours. The mixture is poured into 600 ml. of hot tetrahydrofuran and filtered. 1,2-Diamino-4-(2-cyanoethylthio)benzene is obtained from the filtrate by evaporation.

Workup

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

Sources & evidence

ORD record
ord-46a8a5c11b5c473ca085242c8f3ded77
Source dataset
uspto-grants-1977_01
Patent number
US04002640

Reaction notes

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