Benzene → HCID 12912154, compound

HRID 443691Notes

Reaction equation

HRID 443691 reaction equation
C1C=CC=CC=1.C(N(CC)CC)C.[CH3:14][N:15]1[C:19]([OH:20])=[C:18]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[C:17]([CH3:30])=[N:16]1.[C:31](Cl)(=[O:33])[CH3:32]>O>[CH3:14][N:15]1[C:19]([O:20][C:31](=[O:33])[CH3:32])=[C:18]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[C:17]([CH3:30])=[N:16]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178434069HCID 178434069, compound

Product 1

HCID 12912154HCID 12912154, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a mixture of 20 ml. of benzene and 0.51 g. of triethylamine is dissolved 1.25 g. of 1,3-dimethyl-4-(2-chlorobenzoyl)-5-hydroxypyrazole and 0.4 g. of acetyl chloride is added dropwise at room temperature with stirring. After completion of the dripwise addition, the mixture is stirred at room temperature for 3 hours. After completion of the reaction, water is added to the reaction mixture to dissolve the salts and an organic layer is separated. The organic layer is dried over anhydrous sodium sulfate and the solvent is distilled off. The resulting oily substance is recrystallized from n-hexane to give crude crystalline substance. The substance is recrystallized from methanol to give 1.20 g. of the desired product as colorless prisms melting at 78°-79° C. Yield 82.2%.

Workup

  1. additionIn a mixture of 20 ml
  2. additionAfter completion of the dripwise addition
  3. stirringthe mixture is stirred at room temperature for 3 hours
  4. additionis added to the reaction mixture
  5. dissolutionto dissolve the salts
  6. customan organic layer is separated
  7. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  8. distillationthe solvent is distilled off
  9. customThe resulting oily substance is recrystallized from n-hexane
  10. customto give crude crystalline substance
  11. customThe substance is recrystallized from methanol
  12. customto give 1.20 g

Sources & evidence

ORD record
ord-98bf84d05b7b417a9c8a0bebbb897907
Source dataset
uspto-grants-1981_04
Patent number
US04261729

Reaction notes

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