2-Aminobiphenyl → 2-(o-Biphenylyl)thiophene
Reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[S:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.N(OCCCC)=O>>[C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:15]1[S:14][CH:18]=[CH:17][CH:16]=1Participants
4
Procedure
In a 4-l Erlenmeyer flask were placed 100 g (0.600 mole) of Pfalz and Bauer o-aminobiphenyl, m.p. 49°-51° C., 3000 ml (38.2 moles) of thiophene and 90 ml (0.80 mole) of n-butyl nitrite. The mixture was thoroughly stirred and then allowed to stand at room temperature for eight days. Unreacted thiophene was removed by distillation. The residue was distilled at reduced pressure to give 49.4 g (34.8%) of 2-(o-biphenylyl)thiophene b.p. 138°-155° C. (0.1 mm), ND20 1.6465.