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

HRID 1679475Notes

Reaction equation

HRID 1679475 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-22eed26a7103483e8a2e737a8f118805
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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