O-Phenylenediamine → 4-(2-Aminoanilino)-2,5-dihydrothiophene-3-carbonitrile

HRID 427041Notes

Reaction equation

HRID 427041 reaction equation
O=[C:2]1[CH:6]([C:7]#[N:8])[CH2:5][S:4][CH2:3]1.[C:9]1([NH2:16])[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15]>C(O)(=O)C>[NH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:16][C:2]1[CH2:3][S:4][CH2:5][C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 3266764-Cyano-3-tetrahydrothiophenone

Product 1

HCID 203877024-(2-Aminoanilino)-2,5-dihydrothiophene-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Keto-4-cyanotetrahydrothiophene (80 g, 0.629 mol) and o-phenylenediamine (68 g, 0.629 mol) were dissolved by heating in 1.5 liters of industrial methylated spirit. To the solution, glacial acetic acid (3 ml) was added, the solution then being heated under reflux with mechanical stirring for 24 hours. The solution was then chilled and filtered to give the title product as a solid, m.p. 163° C.

Workup

  1. temperaturethe solution then being heated
  2. temperatureunder reflux
  3. temperatureThe solution was then chilled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-06eafaece82f49d79cd68cad1dfe6c6d
Source dataset
uspto-grants-1979_10
Patent number
US04172831

Reaction notes

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