Benzene → HCID 12912194, compound

HRID 1980388Notes

Reaction equation

HRID 1980388 reaction equation
[CH2:1]([N:4]1[C:8]([OH:9])=[C:7]([C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[C:6]([CH3:20])=[N:5]1)[CH:2]=[CH2:3].C1C=CC=CC=1.C(N(CC)CC)C.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>O>[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([O:9][C:8]2[N:4]([CH2:1][CH:2]=[CH2:3])[N:5]=[C:6]([CH3:20])[C:7]=2[C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])(=[O:42])=[O:41])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178456657HCID 178456657, compound

Product 1

HCID 12912194HCID 12912194, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 180 mg. of 1-allyl-3-methyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole in 6 ml. of benzene and 58.4 mg. of triethylamine is added dropwise 110 mg. of 4-toluenesulfonyl chloride with stirring at room temperature. Then, the resulting mixture is heated under reflux for 1 hour. After completion of the reaction, water is added to the reaction mixture and an organic layer is separated. The organic layer is dried over anhydrous sodium sulfate, the solvent is distilled off and the resulting oily substance is recrystallized from benzene-n-hexane to give 173 mg. of the desired product as colorless prisms melting at 113°-114° C. Further, the solvent is distilled off from the mother liquor and recrystallization from n-hexane gives 26 mg. of the desired product. Total yield 73.9%

Workup

  1. temperatureThen, the resulting mixture is heated
  2. temperatureunder reflux for 1 hour
  3. additionis added to the reaction mixture
  4. customan organic layer is separated
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. distillationthe solvent is distilled off
  7. customthe resulting oily substance is recrystallized from benzene-n-hexane
  8. customto give 173 mg

Sources & evidence

ORD record
ord-8491d56a59aa4ccc9197a655839ff641
Source dataset
uspto-grants-1985_04
Patent number
US04508910

Reaction notes

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