3,4-Dichloroaniline → HCID 20335438, compound

HRID 1706358Notes

Reaction equation

HRID 1706358 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[CH:12]([C:15]([O:17]CC)=O)[C:11]([CH3:20])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[Cl:29])[NH2:25]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[CH:12]([C:15](=[O:17])[NH:25][C:24]3[CH:26]=[CH:27][C:28]([Cl:29])=[C:22]([Cl:21])[CH:23]=3)[C:11]([CH3:20])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 20335430HCID 20335430, compound

Product 1

HCID 20335438HCID 20335438, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The mixture of 0.6 g of 1-(3,4-dichlorophenyl)-3-methyl-4-carbethoxy-2-pyrazolin-5-one, 0.31 g of 3,4-dichloroaniline and 40 ml of xylene is distilled for a few minutes, refluxed 20 minutes and distilled again a few minutes. The cooled solution deposits crystals, which are collected, washed with benzene and recrystallized from ethyl acetate to yield the 1-(3,4-dichlorophenyl)-3-methyl-4-(3,4-dichlorophenylcarbamoyl)-2-pyrazolin-5-one, melting at 255°-257° (dec.).

Workup

  1. distillationis distilled for a few minutes
  2. temperaturerefluxed 20 minutes
  3. distillationdistilled again a few minutes
  4. customThe cooled solution deposits crystals, which are collected
  5. washwashed with benzene
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-67cdae3b3f0b4baa94368a01779c4e14
Source dataset
uspto-grants-1980_06
Patent number
US04207317

Reaction notes

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