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

HRID 1764251Notes

Reaction equation

HRID 1764251 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 litres 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-b47d6d96eb4c4ecca3572f4ea27dd5df
Source dataset
uspto-grants-1978_09
Patent number
US04115568

Reaction notes

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