2-Chloroaniline → N1,N1-Dimethyl-N2-(o-chlorophenyl)formamidine

HRID 453716Notes

Reaction equation

HRID 453716 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[CH3:11][N:12]([CH3:14])[CH:13]=[N:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 72402-ChloroanilineHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 137434N1,N1-Dimethyl-N2-(o-chlorophenyl)formamidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

98% 2-chloroaniline (195 g; 1.5 mol) and 98% dimethylformamide dimethyl acetal (228.2 g; 1.8 mol) were dissolved in toluene (300 g), and the solution was heated under reflux for 4 h. During this time, the internal temperature fell from 96 to 77° C. Thereafter, 15 g of distillate were removed, and the internal temperature rose again during this time to 84° C. Finally, the reaction solution was concentrated on a rotary evaporator at 90° C. and 5 mbar and the resulting brown oil (270.5 g) was fractionated by means of column distillation. The main fraction distilled over at 120° C. and 1.4 mbar and comprised the product in a purity of >99% (determined using area percentages of the GC spectrum).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 4 h
  3. customfell from 96 to 77° C
  4. customThereafter, 15 g of distillate were removed
  5. customrose again during this time to 84° C
  6. concentrationFinally, the reaction solution was concentrated on a rotary evaporator at 90° C.
  7. distillation5 mbar and the resulting brown oil (270.5 g) was fractionated by means of column distillation
  8. distillationThe main fraction distilled over at 120° C. and 1.4 mbar

Sources & evidence

ORD record
ord-10fde5f4168b47e3bc9a6c633a9eba6f
Source dataset
uspto-grants-2013_07
Patent number
US08492558B2

Reaction notes

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