2-Aminobiphenyl → 2-(o-Biphenylyl)thiophene

HRID 46642

Reaction equation

HRID 46642 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]=1

Participants

4

Reactant 3

HCID 70152-AminobiphenylHCID 8030Thiophene2×HCID 10996Butyl nitrite

Product 1

HCID 142439862-(o-Biphenylyl)thiopheneYield 34.8%

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.

Workup

  1. customwas removed by distillation
  2. distillationThe residue was distilled at reduced pressure

Sources & evidence

ORD record
ord-eccd3d4c1897434e80a4312eac06faaf
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Linked notes

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