Benzaldehyde → HCID 641194, compound

HRID 453715Notes

Reaction equation

HRID 453715 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[C:10]1([CH:9]=[N:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[Cl:1])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 72402-Chloroaniline

Product 1

HCID 641194HCID 641194, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

98% 2-chloroaniline (781 g; 6 mol) and 98% benzaldehyde (659.6 g; 6 mol) were dissolved in ethanol (832 g), and the solution was boiled under reflux for 8 h (heating apparatus adjusted to 90° C.). Subsequently, the reaction solution was concentrated on a rotary evaporator at 85° C. and 20 mbar and then fractionally distilled through a distillation apparatus. The main fraction distilled over at 142° C. and 1.3 mbar. 1048 g of the product were obtained in 99% purity.

Workup

  1. temperatureunder reflux for 8 h
  2. concentrationSubsequently, the reaction solution was concentrated on a rotary evaporator at 85° C.
  3. distillation20 mbar and then fractionally distilled through a distillation apparatus
  4. distillationThe main fraction distilled over at 142° C. and 1.3 mbar

Sources & evidence

ORD record
ord-9c8aa666687b4989ab9efe6b22149f8a
Source dataset
uspto-grants-2013_07
Patent number
US08492558B2

Reaction notes

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