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

HRID 1679477Notes

Reaction equation

HRID 1679477 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 four 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 four hours
  3. additionThe mixture is poured into 600 ml
  4. filtrationof hot tetrahydrofuran and filtered

Sources & evidence

ORD record
ord-b745af38226d4d4d930eadfedf48d609
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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