p-Toluenesulfonic acid → HCID 20556953, compound

HRID 1660539Notes

Reaction equation

HRID 1660539 reaction equation
[C:1]([C:6]1[CH:46]=[C:45]([C:47]([CH2:50][CH3:51])([CH3:49])[CH3:48])[CH:44]=[CH:43][C:7]=1[O:8][CH:9]([CH2:41][CH3:42])[C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:40])=[C:17]([CH:39]=1)[NH:18][C:19]1[CH:23]([N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)[C:22](=[O:29])[N:21]([C:30]2[C:35]([Cl:36])=[CH:34][C:33]([Cl:37])=[CH:32][C:31]=2[Cl:38])[N:20]=1)=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2].[C:52](OC(C)=C)(=[O:54])[CH3:53].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:1]([C:6]1[CH:46]=[C:45]([C:47]([CH2:50][CH3:51])([CH3:48])[CH3:49])[CH:44]=[CH:43][C:7]=1[O:8][CH:9]([CH2:41][CH3:42])[C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:40])=[C:17]([CH:39]=1)[NH:18][C:19]1[C:23]([N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)=[C:22]([O:29][C:52](=[O:54])[CH3:53])[N:21]([C:30]2[C:35]([Cl:36])=[CH:34][C:33]([Cl:37])=[CH:32][C:31]=2[Cl:38])[N:20]=1)=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7916Isopropenyl acetateHCID 178458361HCID 178458361, compound

Product 1

HCID 20556953HCID 20556953, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

34 g of 3-{5-[2-(2,4-di-tert-amylphenoxy)butyramido]-2-chloroanilino}-1-(2,4,6-trichlorophenyl)-4-(1-pyrazolyl)-5-oxo-2-pyrazoline (prepared by the method described in German Patent Application (OLS) No. 2,536,191), 25 g of isopropenyl acetate and 0.5 g of p-toluenesulfonic acid were added to 250 ml of benzene and the mixture was refluxed for 5 hours. After the reaction, the reaction mixture was condensated under reduced pressure. Upon crystallization of the residue from a solvent mixture of benzene and hexane, 23 g of Coupler (2) was obtained. The melting point of the coupler was 102° to 108° C.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customAfter the reaction
  3. customUpon crystallization of the residue
  4. additionfrom a solvent mixture of benzene and hexane, 23 g of Coupler (2)
  5. customwas obtained
  6. customwas 102° to 108° C.

Sources & evidence

ORD record
ord-1e5ad509d49746acbf7666956e20e430
Source dataset
uspto-grants-1981_12
Patent number
US04308343

Reaction notes

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