Aniline → N,N'-Diphenylformamidine

HRID 2055772Notes

Reaction equation

HRID 2055772 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 (1 equ.) and aniline (2 equ.) 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. N,N′-diphenyl formamidine (1 equ.) and triethyl orthoformate (2 equ.) are mixed and a catalytic amount of dry aniline hydrochloride is then added. The mixture is heated and ethanol is seen to reflux within a few minutes. The mixture is heated at reflux for 1 hour and then the ethanol is distilled. Following the distillation, anhydrous potassium carbonate is added. The mixture is shaken and then allowed to stand for 2 hours. The reaction mixture is then distilled under reduced pressure. At 93 mmHg, excess triethyl orthoformate is collected at 83-85° C. The pressure is then reduced to 40 mmHg and ethyl N-phenylimdioformate is collected at 117° C. in 95% 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-d750f1907c064cc9ae1cb02e538ceed2
Source dataset
uspto-grants-2008_02
Patent number
US07332553B2

Reaction notes

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