Ethanol → HCID 13064593, compound

HRID 2198828Notes

Reaction equation

HRID 2198828 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13](OC)=[C:12](F)[CH:11]=2)[CH:5]=[C:4]([Cl:19])[C:3]=1[N:20]=[CH:21][N:22]([CH3:24])[CH3:23].[F:25][C:26]([F:36])([F:35])C1C=C(C=CC=1)C=O.C(O)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:26]([F:36])([F:35])[F:25])[CH:11]=2)[CH:5]=[C:4]([Cl:19])[C:3]=1[N:20]=[CH:21][N:22]([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 702EthanolHCID 679903-(Trifluoromethyl)benzaldehydeHCID 13059651HCID 13059651, compound

Product 1

HCID 13064593HCID 13064593, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 9.3 g. of N'-(4-amino-2,6-dichlorophenyl)-N,N-dimethylformamidine (Example 9) and 6.9 g. of m-trifluoromethylbenzaldehyde in 25 ml. of absolute ethanol is refluxed for 18 hours. The solution is evaporated in vacuo to give a syrup. The syrup is extracted into hot heptane. The solvent is evaporated to provide an oil. The oil is dissolved in chloroform and the solution is filtered through a magnesium silicate column packed with chloroform. The column is washed with chloroform until the wash is colorless. The filtrate is evaporated to give a yellow syrup which crystallizes on cooling. The product is recrystallized from n-hexane to give 8.3 g. of the product of the Example as granular yellow crystals, m.p. 62°-64° C.

Workup

  1. additionA mixture of 9.3 g
  2. customThe solution is evaporated in vacuo
  3. customto give a syrup
  4. extractionThe syrup is extracted into hot heptane
  5. customThe solvent is evaporated
  6. customto provide an oil
  7. filtrationthe solution is filtered through a magnesium silicate column
  8. washThe column is washed with chloroform until the wash
  9. customThe filtrate is evaporated
  10. customto give a yellow syrup which
  11. customcrystallizes
  12. temperatureon cooling
  13. customThe product is recrystallized from n-hexane
  14. customto give 8.3 g

Sources & evidence

ORD record
ord-4c07533838a24c4c8366c83bb2df977d
Source dataset
uspto-grants-1982_11
Patent number
US04360466

Reaction notes

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