HCID 788030, compound → HCID 178443050, compound

HRID 2163279Notes

Reaction equation

HRID 2163279 reaction equation
Cl.[Cl:2][C:3]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:6][C:4]=1[NH2:5].[Cl:28][C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[C:30]=1[N:37]1[C:41](=[O:42])[CH2:40][C:39](OCC)=[N:38]1>C(O)C>[Cl:36][C:31]1[CH:32]=[C:33]([Cl:35])[CH:34]=[C:29]([Cl:28])[C:30]=1[N:37]1[C:41](=[O:42])[CH2:40][C:39]([NH:5][C:4]2[CH:6]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:8]([Cl:10])=[CH:9][C:3]=2[Cl:2])=[N:38]1

Participants

4

Reactant 2

HCID 788030HCID 788030, compoundHCID 22753007HCID 22753007, compound

Product 1

HCID 178443050HCID 178443050, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 16 g of the 2,4-dichloro-5-hexadecyloxyaniline hydrochloride obtained in Step (2) described above and 12 g of 1-(2,4,6-trichlorophenyl)-3-ethoxy-2-pyrazolin-5-one was heated to 150° C. and melted. Thereafter, the mixture was reacted at 150 to 160° C. for an hour under a reduced pressure (approximately 20 mm Hg) with stirring while removing the ethanol formed. The reaction mixture was allowed to cool to 100° C. and then 100 ml of ethanol was added thereto. After heating with stirring, the mixture was allowed to cool to room temperature. The precipitate was recovered by filtration. After drying, the precipitate was recrystallized from 100 ml of ethyl acetate to obtain 16 g of the desired coupler. The melting point thereof was 107 to 108° C.

Workup

  1. customThereafter, the mixture was reacted at 150 to 160° C. for an hour under a reduced pressure (approximately 20 mm Hg)
  2. customwhile removing the ethanol
  3. customformed
  4. temperatureto cool to 100° C.
  5. temperatureAfter heating
  6. stirringwith stirring
  7. temperatureto cool to room temperature
  8. filtrationThe precipitate was recovered by filtration
  9. customAfter drying
  10. customthe precipitate was recrystallized from 100 ml of ethyl acetate
  11. customto obtain 16 g of the desired coupler
  12. customthereof was 107 to 108° C.

Sources & evidence

ORD record
ord-026c02e907d144b18d15c03c86fcb334
Source dataset
uspto-grants-1979_01
Patent number
US04133686

Reaction notes

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