Aniline → N,N'-Diphenylformamidine

HRID 1272398

Reaction equation

HRID 1272398 reaction equation
C(OCC)(OCC)OCC.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:18]1([N:24]=[CH:25]OCC)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:12]1([NH:11][CH:25]=[N:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 31214Ethyl orthoformateHCID 111236Methanimidic acid, N-phenyl-, ethyl ester

Product 1

HCID 94888N,N'-DiphenylformamidineYield 80%

Procedure

Thus, a mixture of triethyl orthoformate (1equ.) and aniline (2equ.) is heated at reflux for 2 hours. The ethanol evolved during the reaction is then distilled through a fractionating column. The reaction mixture is then allowed to cool, whereupon it solidifies. Recrystallisation of the solid from toluene yields N,N′-diphenyl formamidine in 80% yield.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. distillationis then distilled through a fractionating column
  4. temperatureto cool, whereupon it
  5. customRecrystallisation of the solid from toluene

Sources & evidence

ORD record
ord-c3dd3cd3ee6e4b1db0ef537825416e85
Source dataset
uspto-grants-2007_04
Patent number
US07208557B2

Linked notes

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