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

HRID 1764288Notes

Reaction equation

HRID 1764288 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-122fa78d89eb49808e8e7c2e1bebf67f
Source dataset
uspto-grants-1978_09
Patent number
US04115574

Reaction notes

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